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Mayfly–December Romance

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Large disparities in lifespans between characters can be problematic, especially if their relationship goes into the romantic field. This plays on the very mundane fact a character will probably be long dead before another is, and the emotional issues it raises. How much this is alluded to is usually related to how concise the story which addresses it is. The most obvious way to address the issue is to even out the age-bracket on either end. In older fiction, characters may be granted immortality, but recently the reverse, making the immortal mortal, is more common.
For the Half-Human Hybrid progeny of these pairings, it's even harder to find a compatible mate lifespan-wise, because generally their lifespan is some sort of average of their parents'. They'll live longer than the mayfly, and shorter than the immortal. Such individuals tend to be rare, so there's no option with "just the right amount of lifespan."
If the immortal is a vampire, they usually have an obvious way around this, but this has a tendency to piss off the would-be mortal or turn them evil, as opposed to the Friendly Neighborhood Vampire the original was.
Can raise Fridge Logic issues in an Anyone Can Die franchise with a high body count, given how few characters in such series even get the chance to live out a full lifespan.
Anime is known for its treatment of the subject due to the Japanese concept of Mono no Aware; roughly, the beauty of transient things.
Subtrope of Age-Gap Romance. May–December Romance is the more mundane version without the mayflies. Compare Reincarnation Romance. Contrast Eternal Love, where both partners are immortal or at least long-lived. See Mayfly–December Friendship for the platonic equivalent. May be a reason for Who Wants to Live Forever?.
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Eternals
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Mary Shelley's Frankenhole: When the immortal Victor Frankenstein was courting Elizabeth (during her wedding reception), he spiked her drink with an immortality potion, which leads her outliving her husband... then her next one. She agrees to marry Victor, realizing she doesn't want to become a widow over and over again.
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A common problem in Natsume's Book of Friends when a youkai and a human fall in love.
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Adventure Time: In the episode "The Suitor" it is revealed that Princess Bubblegum is much older than she appears. In fact, her suitors have been waiting in the castle to court her for a very long time. When Peppermint Butler asks the decrepit suitors how long they've been waiting in line his answers were "87 years", "120 years", and "300 years". While all of them look incredibly old, Princess Bubblegum still looks like an 18 year old. In fact, the suitor chosen to court the princess inherited his father's place in line after he died.
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Klunscomic: Biologically, both Tajer and Miss B are young adults. However, while Tajer is a mortal human, Miss B is thousands, if not millions of years older than her.
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Watchmen: The Immortal Doctor Manhattan is fully aware of the fact that his girlfriend will continue to grow old and he will not. His first girlfriend, Janey Slater, is also aware of this, and it eventually causes the end of their relationship when he leaves her for the much younger Laurie. Of course, Doctor Manhattan knowing beforehand that this would happen doesn't help things.
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One of the eponymous AI tanks in the Bolo universe bitterly reflects upon this when she realises that her commander has been treating her as a human woman, not a multi-thousand-ton, fusion-powered, functionally immortal battle tank, and that she loves him back. She gives no hint of this angst to him and keeps it strictly platonic.
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Tree of Aeons: Pure-blooded elves can live for 500 years, so when they marry humans, it's not uncommon for them to outlive their great-grandchildren. Laufen sits her daughter Lausanne down for a talk after Lausanne's husband passes away; he lived to 100, not a bad run, but Lausanne is still not even middle-aged.
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In This Immortal, Conrad Nomikos and his newly-wed wife Cassandra. The former is functionally immortal with an unspecified number of past identities while the latter is a twenty-year-old normal woman.
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Nicholas Sparks's A Walk to Remember features a young man who marries his high school sweetheart when she's dying of cancer, leaving her dead at the age of nineteen mere months after their wedding while he lives a normal lifespan.
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Eerie Cuties: This was briefly discussed between Layla and her mother, who noted that Layla's aging process would soon become progressively slower, preserving her youthful appearance, while her boyfriend, Kade, would continue to age normally. Maria surmised that he'd likely be in his 40's before Layla physically resembled a 19 year old.
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Spoofed in Girls Next Door, when a certain wangsty sparklepire discovers that not only is his new mouthbreathing target (Sara Williams) already staked out by another glittery, immortal object of fangirl lust, but that their (comically disfunctional) relationship is entirely angst free. He does not take it well, and starts choking on his own Bishie Sparkle.
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Bella is very conscious of this trope and has spent most of the first three books trying to convince her immortal vampire boyfriend, Edward (who is more than a century old stuck in the body of a teenager), to bite her to avoid this. In Breaking Dawn, she does end up turned into a vampire after her pregnancy makes her very sick and the delivery destroys her body.
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The Mighty Thor: Thor had a relationship with a human woman, Jane Foster. His father Odin did not approve. Jane was briefly elevated to godhood but it still didn't work out.
Lampshaded by Doctor Doom when he confronted Asgardian goddess Kelda who wanted to avenge the death of her beloved, Bill.
Thor (2018) #7 reveals that Thor fell in love with a Viking woman named Erika the Red in the 10th century AD, but left Earth to fight in a war and, when he returned, found that 40 years had passed and Erika had died of old age, while Thor had barely noticed the passage of time.
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Played straight in Brigadoon: Marin and Melan, where the young Barrier Maiden was sent to earth for her safety. She's taken in by a kind Japanese family, but her sense of time is much different from theirs, and she barely ages at all before the couple die. She also marries their grandson, and she explains that she would die before him and that she, technically, wasn't human. He doesn't care and they get married anyway. Again, she seems as if she's in her twenties by the time he's lying on her death bed in at least his seventies. In the manga, at least. In the anime, the situation was somewhat different (and in ways, a lot more confusing).
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In Vampeerz My Peer Vampires, Ichika is a human girl, Aria is a vampire. However, Ichika accepts her mortality stating that it could not be helped. However, in chapter 15, it is shown that Aria's blood does have the potential to make Ichika immortal as evidenced by ants getting revived through her blood.
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X-Men villains Mystique and Destiny deconstructed this trope. Mystique doesn't naturally age but Destiny did, and since the two ladies met and fell in love in the early 20th century, Mystique had to helplessly watch her partner grow old, and she would have eventually died of old age had she not been murdered.
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In Bleach, the relationship between Ichigo's parents, Isshin and Masaki, becomes this, once it's revealed that Isshin is a Soul Reaper. An ex-captain Soul Reaper. Keep in mind that Hitsugaya is physically in his early teens, but has lived long enough to be a human's grandfather. The adult-looking Isshin's got to be older than that.
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The Harvest Goddess and the Witch Princess, the Kappa from More Friends of Mineral Town, and Keira the century-old princess sleeping in the mines in the DS games are perfectly okay with marrying the player character, once the requirements are fulfilled. However, the fact that they are long-lived and will be predeceased by their spouse never comes up in conversation.
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Circles: Paulie, the December, and Douglas, the May, are in a May–December Romance. Tragically however, due to Paulie's HIV, Paulie becomes the Mayfly.
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In The Silmarillion:
Thingol (Elf) and Melian (angel). Elves are immortal but can be killed, and Thingol's murder leaves Melian alone and grief-stricken.
Aegnor (Elf) and Andreth (Human). Aegnor pretended not to return her love, so he wouldn't have to watch her age, though it probably broke his heart to do so. He also feared that if the Siege of Angband broke then he would very likely die in battle (and he was right — she outlived him). Since elves reincarnate, Aegnor refused to be reembodied since a world without Andreth was not one he wanted to ever return to.
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Death himself has a rather romantic relationship with Mrs Flitworth in Reaper Man (he gives her diamonds, flowers, and chocolates!). He takes her to a dance just after she dies.
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The Rifter: John (a nearly-immortal God in Human Form) and Ravishan. But the author found a way of making the latter long-lived after all, by the same enchantments that create issusha’im. To her credit, it's well-justified in the overall structure of the novel.
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The Adoration of Jenna Fox has Jenna, who is immortal because she is an Artificial Human, marrying Ethan and having his child before he dies. Jenna says she'll end her life when their daughter reaches a certain age, so she doesn't have to watch her die.
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While it's unknown if the Two Sisters engaged in this in the past, the Lunaverse mentions an off-screen moment where Luna tells Shining Armor that this is the true nature of his romance with Cadenza, and while she will mourn him when he is gone, and move on when she is done mourning, she will never forget him.
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Fire Emblem:
Inverted with Fire Emblem: The Blazing Blade's quasi-canon couple Eliwood and Ninian. You'd think being a 1000-year-old half-dragon would mean Ninian would outlive Eliwood, but in fact abandoning the dragon homeworld makes her die within the next twenty years, as the changes in Elibe itself make the survival of dragons and half-dragons much harder than it used to.
Which leads into the relationship between Eliwood's son, Roy and possible bride Sophia who, like Ninian, is half-human, half-dragon. However, there is no mention of any changes to her lifespan, possibly because she doesn't come from another dimension like Ninian does. If you also accept that Ninian is Roy's mom, then you have the interesting case of a quarter-dragon and a half-dragon. It should be noted that the support conversations between half-dragon Sophia and full dragon Fae also directly discuss this trope, albeit from the friendship angle: Fae will outlive Sophia and all the friends she has made in the game, and she's not pleased at all.
A point that's brought up by both Nowi and Tiki in Fire Emblem: Awakening if they form a relationship with Ricken and the player's character respectively, as both of them are Manaketes and capable of living for thousands of years. Nowi questions Ricken about whether he really wants to marry her when she'd be looking youthful as ever even when he's an old man, while Tiki states that she's aware that she'll have to part with the player long before her life ends, but promises she'll remember him forever.
The Children of the Goddess in Fire Emblem: Three Houses, like Manaketes, live for millennia, so it's assumed that Seteth or Flayn will outlive any of their possible love interests by centuries. The same may be true of Byleth, though due to their unique powers they may be able to control the rate at which they age and live a normal human lifespan.
Surprisingly, this was the opposite for Byleth's parents, with their father, a human, being over 300 years old (albeit thanks to his crest blood), and their mother, an artificial Child of the Goddess, not being expected to live past twenty.
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In Arknights, the side story "Who Is Real" is caused by one of these. Two of the main characters, Dusk and Nian, are the immortal fragments of a dead dragon god named Sui. Dusk, during her wanderings, would fall in love with a mortal woman named Dawn. When Dawn eventually passed away of old age, Dusk was so heartbroken that she used her Anomalous Art to create an entire world within a painted scroll where she could live with a facsimile of Dawn. The storyline of the event begins with Nian asking a couple of her friends to locate Dusk so Nian could drag her back into the real world instead of hiding away in the false reality she'd created.
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According to Breath of the Wild, (Sea) Zora age slower than Hylians. Hylians seem to have similar life expectancies to human, however Zora can be over a century and still be young. This means that Link's and Ruto's relationship from The Legend of Zelda: Ocarina of Time retroactively counts. Ruto arranges herself to be married with Link when they're children. Nothing presumably ever actually came out of it though. As a teenage Ruto has to put aside her feelings due to both of their duties, and Link is sent back in time to before they met afterwards. Link doesn't save her again so it's unlikely she developed her crush in the Child Timeline.
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The Star Trek: Enterprise episode "Exile" features an alien who has already loved his way through a few mayflies, and he wants Hoshi to be the next one.
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Downplayed in New Amsterdam (2008), where the premise is that the main character will be immortal until he finds and weds his true love. Only partly averted, because any relationship with someone other than his true love would fall into this trope, including platonic relationships such as his 67 children. He has mentioned being careful to avoid siring more children specifically because of not wanting to watch them grow old and die before him.
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In Starlight and Shadows, drow Liriel enters a relationship with human Fyodor despite knowing that she will far outlive him.
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The Belgariad:
Sorcerers and others with similar magical abilities or heritage can live hundreds or even thousands of years. This is obviously an issue when they fall in love with normal humans. It’s lamp-shaded in the prequels that sorcerers either have to avoid becoming closely involved with normal humans or deliberately distance themselves when the normal humans become old in order to keep their sanity as even their minds are not capable of dealing with repeated bouts of grief as friends, lovers and loved ones pass away.
The prequel Polgara the Sorceress features one that ended rather badly when Polgara falls in love with a young Wacite Arend, her Champion, when she was nine-hundred-odd years old. Her father hustles her out of the city just before its prophesied demise, leaving Ontrose to die in the fighting. Despite two thousand years and a happy marriage (to fellow sorcerer Durnik averting the trope a second time) she still feels terribly guilty about it and holds the loss of her first love against Belgarath.
The prehistoric romance between the god Issa and his handmaiden Salmissra caused their country no end of trouble when he left the theocracy in her hands... and forgot to make her immortal. Dozens of generations of Legacy Immortality under the machinations of self-serving eunuchs have produced a Decadent Court like none other in the world, and Issa is crushed when he checks in to find that his "handmaiden" is a debauched loon who was crowned for being the best Salmissra impersonator.
The fate of the sorcerer Beldin and normal human Vella is ambiguous, as he transforms them both into hawks and they fly away, never to be seen again.
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The Last Unicorn has two examples of this: one serious, one not. When the tree falls in love with Schmendrick, it's treated as a joke. Several chapters later, Amalthea and Lir fall in love. It's explicitly stated that Amalthea still has feelings for him after she's turned back into a unicorn.
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The Hunger: Ancient, immortal vampire Miriam turns her mortal lovers into vampires, who then live with her for a couple of hundred years. They then wither and age rapidly to a near paralytic state, and she files them away in coffins in her attic. She does show some regret over this.
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Honor Harrington:
Honor herself, and everyone else in Manticore, has ready access to Prolong, a treatment that pushes human longevity up to several centuries...if it's administered at a young enough age. The people of Grayson, the planet which adopts Honor as its own, only get it in the present, and many of the people she gets close to are too old for the procedure and thus she'll outlive them by a considerable margin.
One particularly tragic case did involve romance: Bernadus van Dort and Suzanne Bannister. He was a prolong recipient, and she turned out to be too old for the treatment. What made it worse was that she didn't die at a ripe old age, with her husband still looking young. Her transport ship vanished, probably thanks to a pirate attack. Oh, and their daughters were aboard as well. The whole thing also created a rift between van Dort and Suzanne's brother Trevor, and Trevor's friend Steve Westman, which spills over into the plot of Shadow of Saganami.
Historically, this was also the fate of Treecats, as they have lifespans of 250+ years. Prior to prolong, a treecat who bonded with a human almost always committed suicide after their adopt human died. Only rebonding to another human makes it possible to avoid this suicide.
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Justice League of America: Joe Kelly repeated this in one comic where Wonder Woman is shown taking care of an elderly and dying Batman in a dream sequence.
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My Roommate is a Gumiho: Woo-yeo is almost a thousand years old when he falls for college student Dam.
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In Octavia Butler's Wild Seed, protagonist Anywanyu had many husbands throughout her unnaturally long life, both she and her lovers seemed at terms with this.
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Bruce Coville's Book of... Magic II: Vernan's Dragon involves the immortal King Vernan, and his many, many mortal wives. He solves this problem by making them immortal... but can only do so by turning them into dragons.
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Downplayed in the Miraculous Ladybug fanfiction Spellbound (Lilafly). Being half-fae, Adrien has the capability to live for a very long time indeed, while Marinette is a regular mortal, but he's more concerned about the immediate danger to her life from drawing the attention of a Faerie Court. If they survive for so long that he loses her to old age, he would consider that a good problem to have. And she's still coming to terms with the knowledge that he's not fully human, after a very traumatic reveal.
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On Heroes, Sylar seems to believe that this inevitability is grounds enough upon which he can begin to build a relationship of some sort with Claire. Despite the fact that, at present, she's not even eighteen where he's roughly thirty— and that he's a sociopathic murderer and she hates him with a fiery passion. He promises she'll get bored of trying to kill him one day...
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Mermaid Saga. Even the one relationship that can avoid this has issues thanks to the disparity in emotional age between Yuta (who became immortal 500 years ago) and Mana (sheltered and groomed for immortality).
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Tales Series:
Tales of Symphonia:
You have the option to pair off Lloyd with the half-elf Raine, who will outlive him.
Kratos is a 4000-year-old angel who doesn't age, and his wife was a human woman being slowly eaten away by a mutating Cruxis Crystal. And, of course, she dies before the game even starts.
In the sequel Tales of Symphonia: Dawn of the New World, Emil is revealed to be the summon spirit Ratatosk. Still, both him and Marta decide to be together the rest of her days (if you get the best ending, that is)
Also prominent in Tales of Phantasia, with the half-elf Arche. Even though she's from one-hundred and two years in the past, she's going to live much longer than all of her friends, and even her love interest. It's shown in one of the sequels that in a few hundred years, she still misses Chester.
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In Cafe Enchante, among the love interests, Canus is a few hundred years old while Misyr and Il have already lived for thousands of years and all three of them can potentially live for hundreds and/or thousands of years more, compared to Kotone, who has a regular human lifespan.
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A Diplomatic Visit: Discussed in chapter 8 of the sequel Diplomat at Large, when Luna notes her own long lifespan and Pharynx reminds her he won't live as long, even as a Royal Changeling, since he wasn't born one. Luna, however, tells him she has a solution to that, which he accepts once told. That solution is later revealed in chapter 5 of Diplomacy Through Schooling to be passing the mantle of the Nightmare on to him, making him a Power and thus as immortal as she is.
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In Callahan's Crosstime Saloon, in the story The Law of Conservation of Pain, Rachel is an example of this — an incredibly long-living woman through some trick of biology, she's had several long marriages over her centuries of life. Her biological clock is ticking, though, and by the time she finds her way to Callahan's, she's unable to have children anymore, a fact which drives her to despair.
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Story of Seasons: Trio of Towns adds Inari, a fox-deity that the player can court. As fascinated by humans Inari proves to be, they become rather distraught upon realizing that they are falling for the player character, and that said player character is falling in love with them. Mostly because Inari, already a few centuries old, knows that they will outlive the player character, and is aware how their guardian duties would keep the two from being able to be able to live together like normal couples.
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In the Night Huntress series, this occurs between Bones, the 240-year-old vampire, and Cat, the twenty-something half-vampire. Later, Bones reveals that between her half-vampire blood and the occasional drinking of vampire blood, Cat can live for as long as he can, making this a May–December Romance.
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The Outer Limits (1995): In "Last Supper", an immortal 20-something woman who was born in The High Middle Ages has Rescue Sex with the man who saved her from being experimented on. She unexpectedly returns 20 years later when she's involved with the man's son, forcing her to explain her condition.
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Animal Parade added the Wizard and the Harvest King, male versions of the Witch Princess and Harvest Goddess. The difference is that courting the Harvest King has him show reluctance to open to the player character, and actually marrying him leads to several of his lines driving home the fact that he's well-aware of outliving his spouse, explaining his hesitation.
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In Dance in the Vampire Bund, Akira Regendorf is a teenaged werewolf whose powers of regeneration means he may hope to see his third century before the ravages of time catches up with himnote (the Earth Clan Senate have been confirmed as atypical). However Vampire Monarch Mina Tepes is already in her fifth century and is still working on getting past puberty without modelocking herself in her Super Mode.
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In Fullmetal Alchemist, Van Hohenheim and Trisha Elric have this problem, and he is desperately searching for a way to become mortal so he can die with her. He succeeds. In Fullmetal Alchemist (2003), the problem is slightly different, because he's not so immortal after all.
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In the sequels to New Beginnings Blank page has recurring concerns about how his eventual death will hurt Luna. It's averted when he becomes an alicorn.
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The Legend of Drizzt: Drizzt Do'Urden, in his series of novels by R.A. Salvatore, spends much of the series trying to prevent himself from getting close to his human friend, Cattie-brie, knowing that he will outlive her by centuries, but eventually falls for her anyway.
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In the Star Trek: The Lost Era novel The Buried Age, Jean-Luc Picard enters into a relationship with an alien known as "Ariel" (real name Giriaenn). Ariel is effectively immortal, and has been alive longer than humans have existed as a species. Her relationship with Picard was genuine while she had amnesia; when her memory returned, though, she began stringing the "innocent child" along as part of her master plan. Being as old as she is, she's an complete expert at manipulation, plus her people are naturally designed for it anyway.
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It's been shown in The Royal Sketchbook that Celestia and Luna have both been married multiple times throughout their centuries. They've even had mortal children, which they always outlived. Currently Cadance is married to a mortal unicorn, while Luna marries Twilight, who is an alicorn and is thus long-lived like her. Celestia is initially uninterested in dating but she later falls for Rarity, an unicorn.
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Ray and Mary of Hancock also have to deal with the Mortal/Immortal issue. Although at first after the reveal it seems like it might be a dealbreaker for Ray and the issue is never explicitly resolved onscreen, they are seen at the end together and jokingly reviewing the truth about famous historical figures.
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In the All Souls Trilogy between Diana, a witch, and Matthew, a vampire.
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The Mirrorworld Series: Jacob, who is twenty-four, and Miranda, an immortal fairy. Probably a similar situation between Kami'en and The Dark Fairy.
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In Baldur's Gate II, two of the four romanceable characters (Aerie and Viconia) are full-blooded elves, the longest-lived race around, whereas the Player Character can be of any race. Viconia the dark elf won't even get involved with a (surface) elf character due to racial prejudice. Her epilogue when she's chosen as the love interest reveals that the player character actually outlives her, as she is assassinated by her former people. Conversely, the other two possible love interests (Jaheira and Anomen) are a human and a half-elf, so a long-lived player character will outlive them.
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Wonder Woman Volume 1: Discussed in issue 300 when the Earth-One Diana visits the happy home of the married Earth-Two Diana and Steve and notes that even though "Mrs. Trevor" gave up her immortality to have and raise a daughter with Steve she's still aging at less than half the speed as he. Both Steve and Diana are at peace with this, saying that everyone dies eventually and it's simply a part of life.
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Subverted in The Redemption of Althalus, where the goddess Dweia and human protagonist Althalus fall in love, but the problems are resolved early on when Dweia reveals her ability to control time, letting her and Althalus to stay together as long as time itself exists.
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As with the film series, all Immortal/mortal relationships in the Highlander TV series are this. It's spotlighted in the season one episode "Studies in Light", in which Duncan encounters a mortal woman who was his lover fifty years ago.
In another episode, Methos, the oldest immortal alive, strikes up a relationship with a woman who is not only a muggle, but is dying of an incurable disease. When this is brought up, he invokes the trope.
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Implied to be the case in Dragon Age: Inquisition with Solas if the player pursues his romance with a female Lavellan, and possibly one of the reasons he breaks it off at the end of the game. On top of, well, being the elven god who was purportedly responsible for the fall of Arlathan.
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One of the main plot elements of Crest of the Stars, as the Abh have double the lifespans of unmodified humans. There is greater focus on this in the manga.
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The 100 Girlfriends Who Really, Really, Really, Really, Really Love You has an implied aversion. One of Rentarou's girlfriends is an 89-year-old grandmother who has been rendered The Ageless due to her granddaughter trying to invent an immortality drug. At the moment, her body is locked as that of an 8-year-old, but nothing so far suggests that the drug prevents her from aging; if that's the case, she wouldn't die of old age (assuming such a thing could happen) before Rentarou is old enough to die of old age.
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Discussed in The Inheritance Cycle, in a conversation between Eragon and his cousin Roran. Roran is teasing Eragon about his attraction to Arya, before suggesting that he maybe stop chasing after such an impossible girl and settle down with a human girl instead, particularly since being a Dragon Rider makes him quite the catch. Eragon then specifically brings up how, as a Rider, he will live forever unless killed while his human partners wouldn't, and thus his only options for a lasting relationship that wouldn't pass in the blink of an eye for him are either another human Rider (which is impossible for the moment), or an elf, given elves' longevity as well.
This is even defied earlier, when Eragon has a crush on the female lead, the elf Arya. He learns that she's relatively young for an elf - only a hundred years old. Then he decides to come onto her anyway ... and it muddies the relationship, because despite their closeness and her importance in his life, he really is a child to her, and his asking potentially complicates their working relationship, which has to stay intact. Even if he will live forever, he isn't old now. However, they're able to patch things up and develop a strong and sincere friendship that's important to both of them, and she eventually implies that once he's a few decades older she'll feel less like she's robbing the cradle and be open to something.
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 Discussed Trope
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Katherine Kerr's Deverry series:
Salamander/Ebañy is a half-elf whose wife died and is reincarnated in a new body. (Reincarnation is a big part of the Deverry books.) When he finds her again, she is a teenager, and he's about 100. He sees no particular reason not to marry her again — as he points out to his doubting friends, there aren't that many half-elfs around, and this way they might actually live to grow old together. They don't.
Dallandra and Aderyn, she is an elf, he is human. Made worse by her spending time in the Land of the Guardians, where time runs slower, then a partial subversion when Evandar gives Aderyn an elven life span. Unfortunately he forgets to give him elven youth to go with it.
Completely averted with the human Princess Carra and the elven Prince Dar. Evander remembers elven life and youth this time.
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Discussed in a couple Cracked articles:
"7 Awesome Super Powers (Ruined by Science)", #1 Immortality.
The example from Fred Claus is one of the 6 Horrifying Implications of Classic Christmas Movies.
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The Seven Deadly Sins combines this with Reincarnation Romance. Meliodas is a demon who is functionally immortal, while Elizabeth is cursed to always meet him, fall in love with him, and, should she ever remember her previous lives, die violently three days later so she can reincarnate and repeat the cycle. The anime adaptation included a mention that in one life, she never did remember, and as a result he got to watch her die of old age while he remained the same.
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Zel the elf from Interspecies Reviewers prefers his sex partners less than 100 years old, as past that point their mana starts feeling rotten to him. By human standards, he still Likes Older Women though.
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The Dresden Files: Part of the tension between Harry Dresden and Karrin Murphy stems from this, as she is a vanilla mortal and he is a wizard who will live for several centuries. Murphy even cites this in Proven Guilty as one of the issues in her relationship with him, then brings it up again in Cold Days, pointing out that he has other romantic options that will have a similar lifespan. Dresden, with his typical obstinacy, insists he doesn't care and that - when the two are ready - they'll get in a relationship, fireworks and all. They do, at the end of the next book, Skin Game... then she dies in battle during the Peace Talks/Battle Ground two-part episode/book after that, leaving him in a position that could best be described as 'coping'.
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The long-lived Tiste Andii, Korlat, and the already fairly old human, Whiskeyjack, fall in love in Memories of Ice. In fact, it's stated that Tiste Andii tend to have relationships with shorter-lived races, finding 200 years of marriage to their own kind wearisome and a bit pointless.
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This is pretty common in Supernatural fanfiction, as the immortal Castiel will almost certainly outlive his human True Companions (and, if it's a Dean/Castiel or Sam/Castiel fic, his human lover). Season 8 gave these fics an obvious solution to this issue by making Castiel human; while he regained his angelic powers in later seasons, it's common for Dean/Castiel and Sam/Castiel fics written after season 8 to simply have him lose his grace again. The series finale also set up the alternative solution of Castiel reuniting with Dean and/or Sam in Heaven where they no longer have to worry about human lifespans.
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At one point in Golden Sun: Dark Dawn, Kraden mentions that the reason Rief's teenage sister Nowell never returned to the plot is that she got a crush on Piers and left on a joyride with him. Piers, whose age was a touchy subject even thirty years ago, and whose aging has been slowed further by his exposure to the Golden Sun Event. It's unknown whether Kraden's word is good in this case (he's a known crack-Shipper on Deck), or if Piers reciprocates.
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The example from Fred Claus is one of the 6 Horrifying Implications of Classic Christmas Movies.
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Whateley Universe: Discussed regarding the extremely slow-aging Headmistress Carson at Whateley Academy; she's had three marriages over her seventy years, and while none of the lasted long enough for her to outlive them from old age (the first and third ended in divorce, while the second ended when an old enemy murdered him), she soon realized how much it affected those relationships (at one point, she wistfully notes that she presently looks to be the same age as one of her grand-daughters). She was about ready to give up on relationships when she fell in love with another long-lived ex-hero, the former Tin Man (Langley Paulson, currently head of the Engineering Department).
The topic has mostly been avoided by the students who are in similar circumstances; while some of them are The Ageless (including some who are The Fair Folk, are avatars of gods or god-like beings, have powerful Healing Factors that stop them from aging, or are simply temporally frozen), well, being teenagers, most of them haven't really come to grips with this yet. The ones who seem to have given it the most thought are Tennyo (who is bonded with a humanoid WMD created by the Isokist before the Solar System formed) and Carmilla (an infant Eldritch Abomination), and neither of them are happy with the thought that anyone whom they might be involved with would likely be dead and dust in what to them would be a blink of an eye.
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The two sequels to Sable's Grimoire feature the human protagonist Sable starting a romance with the very long lived elf Lisha or the possibly immortal half-dragon Draken. The angst is limited however, as Lisha is already working on a potential magical solution, Draken isn't really a long-term thinker and Sable himself is still getting his head around the idea of a relationship.
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In Djinn Rummy, an immortal genie falls in love with his human female master, although it's because of a Love Potion.
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Third Time Lucky: And Other Stories of the Most Powerful Wizard in the World: Magdelene's centuries old by the time the stories are set mostly. She keeps having sex with young men (most of whom likely aren't aware of her true age). In most cases though calling it "romance" is stretching the word. She mostly has just brief trysts.
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Discworld:
Death himself has a rather romantic relationship with Mrs Flitworth in Reaper Man (he gives her diamonds, flowers, and chocolates!). He takes her to a dance just after she dies.
Lady Margolotta (vampire) and Lord Vetinari (Actually Not a Vampire) might have had some sort of romance. He suggests the relationship broke up or never really went anywhere because she's "much older", although he still apparently had feelings for her years later. They first met when he was quite young, and she eternally looks like an attractive woman of a certain age. By the time they meet again in Unseen Academicals, he probably looks about as old as she does if not older.
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In Embric of Wulfhammer's Castle , the Duchess can have this sort of relationship with the Good Dwarf and Carmina.
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Though the original creators never alluded to it due to the crackishness of the pairing, shippers of Yuffie/Vincent from Final Fantasy VII have done this trope straight into the ground. Same with Vincent/Tifa...rare as it is.
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Though no romance is confirmed, if Balthier and Fran in Final Fantasy XII are meant to be an Official Couple, then it is quite probable that they will experience this. Viera live three times as long as humes. Fran is probably at least 100. She can expect to be alive for another century or so - long after Balthier is dead.
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The Shiva of Final Fantasy XIV was once a mortal Elezen who fell in love with the ageless Hraesvelgr who loved her in return. Because they knew how short their time together would be, Shiva asked that Hraesvelgr devour her, so that their souls could be eternally bound together. Though reluctant, Hraesvelgr eventually granted her wish.
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Torchwood: Immortal Captain Jack Harkness begins a relationship with the 20-something Ianto Jones. Although Jack's home era is far into the future (the 51st century), has been living through the eras after inexplicably finding himself in the 1940s. He's been alive ever since. Ianto is mortal, and, while Jack can (and often does) die, he will always regenerate. This becomes tragic when Ianto dies.
According to a photograph seen briefly at the end of "Something Borrowed", Jack has had at least one spouse he has outlived.
In "Small Worlds", we see Estelle, an old woman who tells Gwen about how she was in love with Jack's father decades before; turns out it was Jack, and the affection is still obviously there on his end despite his being, physically, several decades younger. His reaction to her death at the end of the episode is heartbreaking.
Children of Earth: "Day One" introduces us to Alice Jack's daughter who looks about the same age as him as she hasn't inherited his immortality.
It's been addressed now, in the radio play The Dead Line.
Also addressed in a conversation in Children of Earth, Day Three. And then, of course, Ianto dies.
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In Sands of Destruction, Kyrie, the Destruct Code, has been alive since the creation of the world and still looks barely past puberty. The human girl he develops feelings for is apparently very normal in regards to her expected lifespan. However, this isn't commented on, perhaps because he has no clue about his identity and their feelings are only made explicit at the end of the final episode.
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Averted and played with in Mnemosyne — the main character is an office lady in her early to mid 30s whose secretary and lover appears to be around half her age, if that. And then we find out the office lady is a Nigh-Invulnerable Badass Normal who won't ever die, which seems like bad news for their relationship, until the secretary admits that she, too, is immortal.
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In Inuyasha, the title character is half-demon and thus is implied to live for centuries, while his love interest is a mortal human. The canon never brings up this fairly obvious problem, not even once, leaving Fanfiction to play with it in various ways. The manga author seems to like to avoid this problem, because it actually always occurs when a demon and a human come together. The demonic parents of Inuyasha and Shiori were killed by evil demons when their children were born straight. What became of the demonic parents of Jinenji and Gyu-oh is unknown. At the time of the plot, they are simply gone.
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Thor: The Dark World: Odin disapproves of his son Thor being in love with Jane Foster for this reason, often encouraging him to forget the mortal and hook up with the goddess Sif instead. Loki also taunts Thor about this, commenting that Jane will be long dead after a "mere" 100 years.
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In Homestuck, the fact that she's dead and has existed that way for an uncountable amount of time, however much she may look like a normal teenage girl, is why Aranea tells Jake that a relationship between them couldn't work. He maintains optimism regardless (even thinking to himself that it might work if he dies, betraying perhaps worrying faith in Death is Cheap holding true indefinitely), but even aside from the age disparity Aranea isn't really interested in him and probably only brought it up as a more polite way of rejecting him.
The higher up the hemospectrum a troll is, the longer their lifespan. While someone at the low end (red, orange) might live a few dozen sweeps, someone at the high end (blue, violet) has a lifespan bordering on millenia. Any highblood in a relationship with a lowblood will definitely see several deaths of those they cared about. Mindfang (Vriska's ancestor) notes in her journal that the Summoner (Tavros' ancestor), who was prophecised to start a relationship with her and eventually kill her, most likely hadn't even been born yet at the time of writing.
When Sburb players go God Tier, they achieve immortality. Not everybody reaches God Tier, however, and sometimes the immortal teens date the mortal ones. Examples of this include Dave and Terezi, Rose and Kanaya, Davesprite and Jade, and Dave and Karkat.
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In the sequel Tales of Symphonia: Dawn of the New World, Emil is revealed to be the summon spirit Ratatosk. Still, both him and Marta decide to be together the rest of her days (if you get the best ending, that is)
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The Fault in Our Stars: Played with on the scale of an average human lifespan. Hazel, the sixteen-year-old protagonist, diagnosed with terminal cancer, has an uncertain number of years to left to live, but probably not many. Then she meets and falls in love with a seventeen-year-old Augustus, who is well into remission and will likely live a normal number of years. However, Augustus' cancer recurs, every reader's heart breaks, and Hazel is the one left behind by a lover's death.
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The Twilight Zone (1959): In the episode "Long Live Walter Jameson", a man who appears to be in his thirties or forties is revealed to be thousands of years old. He leaves his wife to prevent her from discovering his secret, but she tracks him down anyway when she is old and he is still young.
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 The Twilight Zone (1959)
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Infinity, Inc.: A subplot of the "Stream of Ruthlessness" story arc involved Earth-2's Wonder Woman seeking a means to restore the youth of an aging Steve Trevor, whom she had married after World War II.
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Tolkien's Legendarium:
These happen several times in the form of rare but significant elf-human pairings. Elf-human mixed couples overall are very rare (known are five and a half, and only three got together permanently). The main angst isn't just because elves live forever and humans don't — the two races do not share the same afterlife. Elves, even if killed, travel to the Undying Lands in the west and are usually granted resurrection, eventually. Humans, upon death, disappear from the world and their fate is unknown. And Elves by nature mate for life, so they usually can't get over it and marry one of their own kind afterwards.
In The Silmarillion:
Thingol (Elf) and Melian (angel). Elves are immortal but can be killed, and Thingol's murder leaves Melian alone and grief-stricken.
Aegnor (Elf) and Andreth (Human). Aegnor pretended not to return her love, so he wouldn't have to watch her age, though it probably broke his heart to do so. He also feared that if the Siege of Angband broke then he would very likely die in battle (and he was right — she outlived him). Since elves reincarnate, Aegnor refused to be reembodied since a world without Andreth was not one he wanted to ever return to.
Beren and Lúthien: Beren (human) and Lúthien (half-elf, half-angel). When Beren dies, his wife chooses to become mortal so they are always together.
The Fall of Gondolin: Tuor (Human) and Idril (Elf). It is rumored that Tuor supposedly became immortal.
The Lord of the Rings:
Aragorn (Man) and Arwen Undómiel (Elf), daughter of Elrond. During the book Aragorn is 88 (young for a human of Númenórean ancestry), while she is 2798 years old. And when they first fell in love, he was 49 and she was still over 2700 years old.
Imrazôr, a Númenórean who settled at Dol Amroth, and Mithrellas, a Wood Elf who got totally lost in the mountains when her people fled from the Necromancer in south Mirkwood. He and his folk sheltered her and they got married, but after having two half-elven kids she just...got up and left him. Elves aren't inclined to marry people they don't love, and there's no suggestion that he married her against her will, so maybe she just didn't want to watch Imrazôr and the children die of old age.
Applied tragically with the Kings of Gondor. Valacar, the grandnephew of the King of Gondor at the time, visited Rhovanion and wed Vidumavi. Vidumavi was a princess of the Northmen of Rhovanion, and at the time of her marriage was much younger than Valacar. Vidumavi lived a very long time for one of her own people, but because she had no Númenórean blood, she grew old at a much faster rate than Valacar - she died before he ascended the throne. The Men of Gondor feared that their son Eldacar would not live as long, and this instigates a civil war in Gondor. (Eldacar inherits Valacar's longevity and lives to be 235 - only three years less than his father. He also inherits the fearless spirit of his mother's people.)
The Fall of Númenor: this trope played in the marriage of Aldarion and Erendis on Númenor, lost home of the Dúnedain. Númenóreans had a lifespan about three times that of ordinary humans, but those of the royal house lived about twice as long. Aldarion was the 6th king of Númenor; Erendis his wife was not from the royal house. She was also much younger than him, but still most likely to die first. Aldarion's long lifespan and his tendency to make multi-year voyages while Erendis continued to age (relatively) rapidly drove a massive, nasty wedge in their relationship. Their problems in turn embittered their daughter, the future queen Tar-Ancalimë. Erendis dies in Second Age 985, over a century before Aldarion dies. Aldarion lived to be 398; Erendis died at only 214. She did drown herself, but she was already old aged by then. Ancalimë inherits her father's longevity and actually lives even longer than him - she dies at the age of 412.
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The Mortal Instruments:
Alec Lightwood is eighteen and dating Magnus Bane, who is an immortal warlock and over 400 years old. This problem is highlighted in the second half of the series, when Alec's attempt to find a way to make Magnus mortal strains their relationship.
At first it seems to be the same with Simon and Isabelle, because he is a vampire, and she is a shadowhunter. However, at the end of City of Heavenly Fire, Simon is transformed back into a human, and a short time later he becomes a shadowhunter.
In the prequel The Infernal Devices, this is the fate that plagues Tessa. Like Magnus, she is an immortal warlock (well, warlock-nephilim hybrid) stuck in the body of a teenage girl. In the 1870s, she falls in love with Will and Jem, both whom are mortal shadowhunters. After Jem becomes an immortal Silent Brother, she marries Will and they start a family, but she does not grow old with him. After he dies of old age in the 1930s, she leaves the family for good, unwilling to see her children, grandchildren, and descendants die before her eyes. Seventy years later, Jem is freed from his duty and restarts his relationship with Tessa, but both know that, eventually, she will outlive him as well.
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World of the Five Gods: In Demon Daughter Penric and Nikys learn that their marriage is one because Desdemona has been using uphill magic to stop Penric's aging process. He asks Nikys if Desdemona should let him age naturally and she says no.
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Also prominent in Tales of Phantasia, with the half-elf Arche. Even though she's from one-hundred and two years in the past, she's going to live much longer than all of her friends, and even her love interest. It's shown in one of the sequels that in a few hundred years, she still misses Chester.
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In Maoyu, the Demon Queen is in love with the human Hero and has been since he was just a baby, as she doesn't seem to age. Hero claims he doesn't return the Demon Queen's romantic overtures because of their drastically different lifespans. Although, that's mostly an excuse since he's hilariously shy around women.
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Persona 3 The protagonist (official names Minato Arisato/Makoto Yuuki/Sakuya Shiomi) to any of the romanceable girls in all the releases of P3, due to becoming the Great Seal at the end. By extension, the female protagonist (official name Kotone Shiomi, but the fandom more often calls her Minako Arisato), to any romanceable guy except Shinjiro in the PSP release.
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A bit of a technicality, but in Persona 4 Golden, you can romance Marie, who is later revealed to be a goddess. While not stated in-game, this essentially means she can't die (at least, not by natural means).
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There's a particularly mean instance of this trope in Yona of the Dawn, between the immortal Zeno and his wife, Kaya. When they met, the mayfly was already fatally ill, and died young. Zeno is around 2,000 years old by the time of the series, but she didn't even live out her natural lifespan.
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The Xanth novels are full of this : X(A/N)th (male demon)/Chlorine, Demetria (female demon)/Veleno, Jewel (nymph) / Crombie, and others. Averted, as Xanth is also absolutely full of Fountains of Youth. And X(A/N)th, being literally omnipotent can do anything he damn well pleases, including extending a human's life indefinitely.
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Undertale discusses the trope on a child to parent relationship instead of romance in the Playable Epilogue if you get the Golden Ending. Gerson tells Frisk that even if Toriel and Asgore adopted them, they would certainly outlive Frisk since Toriel and Asgore are boss monsters and cannot age if they don't have children of their own. The trope can be played straight if you choose to have Frisk live with Toriel as her adopted child or avert the trope by having Frisk go on their own adventures while keeping in touch with Toriel and the others.
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Pita-Ten being an angel Misha is extremely long lived or immortal. This is only an issue in the manga but not the anime where she fell in love with Kotaro's great uncle Kotarou who commits suicide so he can spend his life with her only for that not to be the case. Kotaro is the reincarnation of Misha's love which is why she greets him at their first meeting with 'Let's go on a date!' she's waited some 80 years to see him. Since that isn't the case in the anime, it makes her seem more of a Cloudcuckoolander.
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On Wizards of Waverly Place, Justin and Juliet. She may have been joking when she talked about Caesar but she's been to well over five hundred proms.
When she talks about her relationship with Mason during the finale of that arc, she says she loved him a 'long time ago' - 'Like, before America was discovered'. Which would mean that this trope applies to Alex and Mason's romance too.
Actually several Wizards are shown in the series who are several hundred years old, and one confirmed case of making to several thousand. While its never confirmed that this applies to all Wizards, its certainly possible so this might not be an issue.
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Code Geass: The Prepared Rebellion has Lelouch and C.C. enter a romantic relationship. C.C. is continuously haunted by the fact that Lelouch will eventually die while she never will. This turns out to be part of why she sets him up with other women: so that he can have romantic partners who can grow old with him.
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In Dan Simmon's Hyperion, Merin and Siri from the sub-story, "The Consul's Tale", are engaged in a Mayfly December Romance where Merin, who is a crew member on an interstellar construction ship responsible for building a farcaster gate above Siri's homeworld of Maui-Covenant, must watch his love progressively wilt away as he travels back and forth to the planet at relativistic speeds, all the while remaining young himself.
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In Holly Black's Modern Faerie Tales there is unbelievable quantities of this, most notably in Valiant between Val and Ravus, who actually comes out and says that she will be dead in "one faerie sigh", but they are still hooked up.
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The hero and protagonist Naoto from Kidou Keiji Jiban have this with a woman who's actually one of Biolon's rejected experiments. Firstly because the girl was basically made of raw kindness, which Biolon, being an evil empire, can't tolerate; secondly because she have the power to purify monsters. Naoto, as Jiban, saved her, gave her the name "Pearl" and they quickly reaches the romance territory, before learn she's dying. Pearl sacrifies her last forces to save Jiban from Biolon's latest monster, leaving Naoto heartbroken.
Naoto himself is this to his partner and veteran at the police department, Yoko. Being a revived-turned-into-a-cyborg detective/Robocop expy, and some sort of secret agent to the secret police's top dogs, Naoto/Jiban could outlive or even live less than her. With Yoko in love with Jiban and totally unable to see through Naoto's Clark Kenting until the very last episode, after Biolon's defeat, Naoto chooses to travel around the world, to learn and live as much as his lifespan as a cyborg ables him.
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In The Wolverine, the nigh-immortal Logan becomes involved with Mariko, who's around her twenties in the present day. Logan leaves at the end to continue his journey despite finally coming to terms with Jean's death.
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This subject causes much angsting in the Dragonlance novels, in which Tanis Half-Elven loves both an elf who would long outlive him and a human who would die while he was still young. In case people want to know, he chose the elf, who outlives him due to a more mundane reason. Although it ironically would have actually worked out if he had chosen the human; as he seemed to have started aging at a human rate once he was more than 100.
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TwoKinds: The average lifespan of a keidran seems to be between 20 and 25. Trace (a human) briefly attempts to find a way to extend the life of his keidran lover Flora before giving up and deciding to make the most of the time they have.
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The film "May Flowers" made with The Movies features a romance between a normal human man and a woman (the title character) who is an ancient species, timeless but not ageless. Over the course of a year she ages an entire lifetime and dies at midnight every New Year's Eve only to be reborn as a baby seconds later. May finds husbands to take care of her during this time but does not stay married to them for more than 50 years.
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Used as a punchline in Ultra Fast Pony. Celestia is immortal, and remarkably blasé about the number of relationships she's had over the years. On the other hand, she does try to encourage her current crush (Twilight Sparkle) to become immortal as well.
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Susanna Clarke's Jonathan Strange & Mr. Norrell: In "Tom Brightwind or How the Fairy Bridge Was Built at Thoresby", the eponymous character has one of these with his human wife, but it sours due to his fairy fickleness: "At fifteen... Tom had constantly compared her to a kitten. In her twenties she had been a swan; in her thirties a vixen; and then in rapid succession a bitch, a viper, a cockatrice, and finally, a pig. What animals he might have compared her to now no one knew. She was well past ninety now and for forty years or more she had been confined to a set of apartments... while her husband waited impatiently for someone to come and tell him she was dead."
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All of the love interests for Obey Me! – One Master to Rule Them All! are demons, who are at least a few centuries older than you, the human protagonist.
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The Kindness of Devils: This is one of Hardestadt Delac's main emotional conflicts—especially within Loves Lost And Found. He's thousands of years old and doesn't physically age, while all of the lovers that he's had in the past are all mortal and end up dying from natural causes.
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Deconstructed on both sides of the relationship in The Myth of Link & Zelda: Breath of the Wild with Link x Mipha, especially since they have a daughter. For Link, he lives with agony knowing that he won't live nearly as long as his lover or his daughter, especially because Link will die before Lochlia even grows up. For Mipha, she suffers the pain of knowing that her daughter will largely grow up without her father. She remedies this by keeping diaries, one of which is exclusively about Link.
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Zigzagged in Dungeons & Dragons. While half-elves tend to have somewhat downbeat childhoods, their parents can apparently have quite happy lives together. The human is attracted to the elf's grace, the elf to the human's energy. It's implied that the human gets a partner who doesn't age for the duration of their relationship, and the elf gets a satisfying if short-lived (for an elf) tryst without any worries about bad breakups (assuming their human partner dies of old age). Other half-races, though, either play it straight, tending to come about because of Mayfly December Romances (half-dragons—even an elf will be in their grave for millennia by the time a dragon lover dies), or in the few exceptions avert it entirely. In the case of half-orcs, it's reversed, since orcs have far shorter lifespans than humans, and are more likely to die by violence.
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In the Mortal Kombat franchise, Earthrealm warrior Liu Kang and Edenia princess Kitana fell in love, but even if it had worked (both perished in the events of Mortal Kombat 9) it would have ended up this way; she was already ten-thousand years old, at least and would have outlived him several times over. Mortal Kombat X has them reunited and playing the trope more or less straight as the Ruling Couple of the Nether-Realm, the Evil Power Vacuum left behind by the death of Quan Chi and the permanent incapacitation of Shinnok.
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Any of the relationships in Baldur's Gate III can become this is the Player Character is an elf, since they would then long outlive their lover. A relationship with Astarion will always fall under this trope, with Astarion as the December and the PC as the Mayfly, since he's a vampire spawn, and therefore, immune to aging.
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Connor MacLeod's first love was a mortal woman named Heather in 16th-century Scotland. They were married for 53 years until her death by old age in 1590.note Heather's age is never stated, but judging by the actress's age in this film and Highlander: Endgame it appears she lived to her mid-seventies. And this was still only a tiny portion of Connor's own immortal lifespan.
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In Tuck Everlasting, not-actually-17-year-old Jesse Tuck tells Winny to drink magic water to gain Immortality when she reaches that age. She gives the water to a toad, ages normally, lives a happy life and dies. Jesse's older brother Miles was once married. When his wife realized that she aged while he stayed twenty-two, she accused him of selling his soul to the Devil.
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Several times in the Symphony of Ages. The Cymrians live shorter lives with each generation, starting with immortality at generation one. This presumably causes true mayfly romances, but the most visible case is Tristan Steward and his consort Prudence. While they grew up at about the same rate, she starts showing her age and he remains youthful. A much more complicated version arises among Rhapsody, Ashe, and Achmed. Rhapsody, a first-generation Cymrian and lirin, will live forever. So will Achmed. Ashe, however, is part dragon and a third generation Cymrian, granting him a lifetime that will probably last a few thousand years more before he either dies or reincarnates as a full dragon (somehow presumed to end their romance, although other dragons have loved humans before). Achmed loves Rhapsody, or at least believes she is the only possible suitable mate for him, but is content to wait millennia for Ashe's eventual removal. (Somewhat surprising, given that he is a cold-hearted assassin and probably quite capable of killing Ashe if he felt his need for Rhapsody required it.)
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In the semi-revisionist fantasy webcomic Errant Story, it was fashionable for some time in the past for the immortal elves to take on human lovers, so that they can experience the mourning, sad joy of seeing their lover grow old and die (especially since relationships between two immortal elves inevitably resulted in the two getting bored with each other over the decades or centuries); apparently this was their culture's take on mono no aware. Elves, in this story, have a lot in common linguistically and culturally with Japan. Jon and Sarine go down this path in the end. The story concludes with Sarine visiting Jon's grave with their half-elf daughter.
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Tayutama the main character expects this trope to happen to himself with his wife Mashiro, only for the opposite to happen when her body is weakened too much and she's forced to sleep a century or two to regenerate, effectively having her 'die' while he's young. The odd ending probably recreates the trope straight but isn't explored.
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Any romance with the Edels in Elemental Gelade falls into this. Aside from a single-episode plot, this is mostly ignored.
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In Expecting Someone Taller, most of Malcolm's romantic entanglements after receiving the Ring fall into this category, especially his eventual engagement to the Valkyrie Ortlinde.
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Storm Clouds And Grey Skies:
Leia is a mermaid in love with a human woman. Mermaids can live for 300 years. However, when Claire asks Leia her age, she clarifies that she's the same age as Claire.
The several thousand year old Harvest Goddess mentions being in love with a normal human, Jill.
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This is actually a very integral part of Vampire: The Masquerade and Vampire: The Requiem. Part of what causes vampires to slowly turn more and more inhuman in attitude is the fact that any human relations a vampire has will eventually die. This either slowly drives them mad from despair or they simply stop bothering with considering humans anything more than toys or lunch. Vampires who try to fight this dissolution of humanity tend to be pretty unhappy.
Keeping ghouls (humans with vampire blood in their system) doesn't help either. They don't age, but they tend to go insane over decades or centuries for the same reason that vampires do (although slightly faster).
And if you try to go all the way and try to make your special someone a vampire like you...well, it's a crapshoot at best, but I Hate You, Vampire Dad is very prone to rearing its ugly head.
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In Dæmorphing, Tom becomes a Hork-Bajir, who only live for about twenty years, and then falls in love with a human called Ruby.
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In Secret City nigh-immortal Santyaga is loveable womanizer, and due to lack of females of his own race this trope is inevitable. It is also played as Tear Jerker in one of the book, when he visits his current love, Susanna, after her retreat to nature because of old age. While he's sad, she claims, that she's happy, and that this situation allowed her to live 3 lifes - before, with and after him, which is even he cannot achieve.
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Stefan and Elena from The Vampire Diaries are another example of an immortal/mortal case. Stefan is a 164 year old vampire and Elena is a 17 year old human girl, who will grow old and eventually die. Stefan is immortal, will never age, cannot grow old and is immune to all human illnesses. Therefore, Stefan's survival rates are significantly much higher then Elena's, who is a vulnerable human. Elena is susceptible to human weaknesses such as illness, aging and possible death. However, despite the difference in species and age difference, Stefan and Elena don't seem to mind. Their love for each other seems to transcend all barriers. Although, due to the differences in age and species, there has been some tension between Stefan and Elena. Stefan and Elena have talked about their age difference and also, the possibility of Elena choosing immortality in order to spend an eternity with Stefan. However, Elena has told Stefan that even though she loves him, she doesn't and never wants to be a vampire and would rather stay human, grow old, have children and live a normal human life. However, the age difference and the concerns over Elena's safety and vulnerabilities as a human don't seem to be a problem any longer now that Elena has recently become a vampire.
Same goes for Damon and Elena, again with these particular problems disappearing once Elena is turned.
Jeremy and Anna were well on their way to this trope too.
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Aang and Katara in Avatar: The Last Airbender. The former is 112 years old (although he's been frozen in an iceberg for 100 of those years) and Katara is 14. This is justified, however, since Aang hasn't had any experiences beyond the years he lived out, so mentally, he isn't really older than Katara (except for the wisdom he was taught as an airbender monk). This explains why his conscious lifespan was way shorter than Katara's in The Legend of Korra, where he is dead long before Korra's adventure even begins. Then again, it was pretty obvious that something like that would happen, considering the fact that the previous Avatar in the cycle must die for the next Avatar to be born. However, if Aang hadn't had his lifespan cut short by being frozen, this trope would be in full swing as Avatars are exceedingly long-lived (the oldest Avatar mentioned in canon, Kyoshi, was 230 at her death).
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Zyuden Sentai Kyoryuger had immortal Deboss villainess Candelira fall for Nossan. The difference in their lifespans is probably the reason for her choice to leave him behind at the end of the show so she can start a new life Walking the Earth and helping humans. It's shown in the sequel movie that a hundred years later she is still alive and hasn't physically aged, while he is long dead and she is now the mentor to his great-great-nephew.
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In the Star Trek: Deep Space Nine episode "Chimera", the changeling Laas brings up this trope while trying to convince Odo (a changeling whose species has an incredibly long lifespan) to leave Kira (a Bajoran with a roughly human-like lifespan) in order to join Laas in locating the rest of the Hundred.
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The Legend of Zelda:
According to Breath of the Wild, (Sea) Zora age slower than Hylians. Hylians seem to have similar life expectancies to human, however Zora can be over a century and still be young. This means that Link's and Ruto's relationship from The Legend of Zelda: Ocarina of Time retroactively counts. Ruto arranges herself to be married with Link when they're children. Nothing presumably ever actually came out of it though. As a teenage Ruto has to put aside her feelings due to both of their duties, and Link is sent back in time to before they met afterwards. Link doesn't save her again so it's unlikely she developed her crush in the Child Timeline.
In Breath of the Wild itself, Mipha was the Zora princess and she fell in love with Link, whom she notes at one point looked grown-up faster than she did. She even wished to marry him. There's also a side quest where you can enforce the trope by getting a young Zora girl and a Hylian man together; said Zora girl is the daughter of one of Link's Childhood Friends named Kodah who was in a Love Triangle for his affections with Mipha, but Link's century-long slumber in the Shrine of Resurrection and Kodah finding a Second Love put an end to this dynamic.
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Steven Universe:
Occurred in the backstory between Steven's parents, his father being a normal man and his mother an immortal Starfish Alien. She even explicitly tried to push him away at first because she expected to outlive him, and didn't want to get in the way of his dreams. And then Rose for all intents and purposes died in childbirth before Greg turned thirty.
In "Mr. Greg" Pearl talks about Rose, mentioning she'd had plenty of human lovers before, but none of them connected emotionally (or romantically competed with Pearl) like Greg did.
Steven himself may or not be immortal, and has a budding romance with his human friend Connie. In "Steven's Birthday", Steven discusses an especially problematic variation of this trope when he discovers he may be growing up very slowly or not at all:
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Inverted with Fire Emblem: The Blazing Blade's quasi-canon couple Eliwood and Ninian. You'd think being a 1000-year-old half-dragon would mean Ninian would outlive Eliwood, but in fact abandoning the dragon homeworld makes her die within the next twenty years, as the changes in Elibe itself make the survival of dragons and half-dragons much harder than it used to.
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Tales of Symphonia:
You have the option to pair off Lloyd with the half-elf Raine, who will outlive him.
Kratos is a 4000-year-old angel who doesn't age, and his wife was a human woman being slowly eaten away by a mutating Cruxis Crystal. And, of course, she dies before the game even starts.
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Mass Effect: The prolonged lifespan of the asari — they can reach about a thousand years of life — has colored their relationships with most of the other species, along with their ability to mate with anything. In contrast, humans, turians, quarians, or batarians can reach 150 at the setting's level of medical tech, and drell can get up into their eighties. Only with krogan, who have a similar lifespan to asari, is this not an issue. Salarians, meanwhile, are lucky if they reach forty. Liara explains that asari who enter into physical and emotional relationships with members of other species do so fully aware that they will outlive their partners, and take a "long view" of the relationship.
The children from such a relationship are always asari — in fact, most asari are the products of such relationships, as there is a stigma attached to being a "pureblood" — which in turn means that most Asari lose at least one parent very early, and salarian parents won't even see their children reach adulthood. This is illustrated by an elderly 35-year-old salarian and his 60-year-old teenage asari stepdaughter in the second game. Another asari asks what species her friend's father was, is told he was a salarian, and delicately says "Oh, so you didn't get much time with him."
One asari mentions this as a reason she's hesitant to get it on with a krogan. Krogan have at least as long of a lifespan — there's mention of one having "millenia" of experience — as asari, making it a big commitment. With humans "you just stick it out a century, and they die". Shepard is less than amused. The couple do get together and have a daughter between games... only for the korgan to die in combat. They got less than a year together.
In one particular mission you have to get a fish for a krogan at the Citadel. In the shop, you can hear a turian and asari talking about getting a fish, and the turian says that maybe they shouldn't get a fish because they only live for a few years. The asari tries to use this as an opportunity to broach the lifespan topic, but her parter isn't having it.
Another possible example is the relationship between Commander Shepard and Thane Krios. One of the first things that Thane tells Shepard is that he is dying of a terminal disease and has only months to live. The fact that Shepard/the player can choose to pursue this relationship anyway, fully aware of this, puts it in this category. In the third game he dies from a combination of getting stabbed by Kai Leng and the final stages of his Kepral's Syndrome if he didn't die in the suicide mission. Liara can comment on this in Lair of the Shadow Broker, comparing Shepard's relationship with Thane with a typical asari/non-asari relationship, and encouraging her to treasure whatever time they have together.
Liara herself is an example of this. She is very young for an asari, but even so, Shepard will most likely only be around for around the same time as she has lived thus far. This is the asari equivalent of getting married at twenty and one partner dying at 40, while the other lives to be 150, or more like comparing the lifespan of a dog to a human. If Shepard chooses the Control ending, however, s/he becomes effectively immortal, inverting the relationship! In Lair of the Shadow Broker, she'll even mention she's only just about to turn a 109 (and typically, asari can live up to a 1000 years). Won't stop a faithful Shepard from proposing a Babies Ever After ending.
During the third game there is a fleeting mention of asari-vorcha offspring. Vorcha live twenty years if they're lucky and tend to be brutal and violent. If adopted and "socialized" they're much calmer and easier to get along with, and the premier institution devoted to "socializing" vorcha is asari-run, making it a distinct possibility that some of those pairings involved Partner Husbandry.
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Gunnerkrigg Court:
Jones, a perfectly immortal Time Abyss precisely as old as the Earth, is in a relationship with the Empowered Badass Normal James Eglamore. She has had numerous similar relationships throughout history; although she claims to have no feelings or emotional impulses of any kind, Antimony disputes that based on her drive to seek companionship, and her human partners don't seem to have any complaints.
In an unconventional example, Antimony's maternal bloodline dies several years after having a child thanks to the mother's life force and spirit migrating into the daughter. Anthony, a human father, labors for years without success to prevent this.
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In The Host (2008), Wanderer is an alien soul who is thousands of years old. She proceeds to fall in love with a human man. However, since she is in a human body, she can age and die naturally alongside him.
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The Heartstrikers: Marcie and Julian are in a relationship, despite Marcie being human and Julian a dragon. While they are about the same age (Marcie is initially slightly annoyed that the first dragon she meets isn't some ancient bastion of knowledge but is actually slightly younger than her), he can easily reach a thousand years and has no theoretical limit to his lifespan, while she shouldn't expect to live longer than a hundred. Both dragons and humans remind them of this several times over the course of the story, advising them to break it off, but they refuse. In the Distant Epilogue, Marcie mentions that one of her colleagues is working on Immortality, and she plans to shamelessly bum it off him the second he finishes it.
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Jack Bonner and Kitty who is an alien in Cocoon.
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Nightmare Time has a romance between the immortal Miss Holloway and the mortal Duke Keane. This causes some angst for Miss Holloway, watching his reaction as she has to fake her own death to avoid any suspicion of her own immortality.
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Maquia: When the Promised Flower Blooms: The Iorph live for centuries and live apart from mortals. Elder Racine warns Maquia against loving an outsider as she will be truly alone if she does. This knowledge is implied to be due to Barlow possibly being her half-Iorph son. The director later revealed those Iorph who survived the Mezarte attack integrated with human populations and many eventually married and had children.
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In The Sims 3: Supernatural, this can happen when normal Sims marry fairies or vampires, since they both have lives that are 5 times that of a normal sim.
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In Cheating Men Must Die, professional transmigrator Su Lüxia takes fifty years of leave to remain in her assigned world after her mission is complete. She eventually marries Gu Chen, a character from the world, but she never ages a day while he continues to age normally throughout their marriage. She's visibly saddened while looking at footage of his later years after her leave is up, and she comments that she won't date in modern-themed worlds anymore because she's unable to do something as basic as growing old with her mortal partners.
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The Lord of the Rings:
Aragorn (Man) and Arwen Undómiel (Elf), daughter of Elrond. During the book Aragorn is 88 (young for a human of Númenórean ancestry), while she is 2798 years old. And when they first fell in love, he was 49 and she was still over 2700 years old.
Imrazôr, a Númenórean who settled at Dol Amroth, and Mithrellas, a Wood Elf who got totally lost in the mountains when her people fled from the Necromancer in south Mirkwood. He and his folk sheltered her and they got married, but after having two half-elven kids she just...got up and left him. Elves aren't inclined to marry people they don't love, and there's no suggestion that he married her against her will, so maybe she just didn't want to watch Imrazôr and the children die of old age.
Applied tragically with the Kings of Gondor. Valacar, the grandnephew of the King of Gondor at the time, visited Rhovanion and wed Vidumavi. Vidumavi was a princess of the Northmen of Rhovanion, and at the time of her marriage was much younger than Valacar. Vidumavi lived a very long time for one of her own people, but because she had no Númenórean blood, she grew old at a much faster rate than Valacar - she died before he ascended the throne. The Men of Gondor feared that their son Eldacar would not live as long, and this instigates a civil war in Gondor. (Eldacar inherits Valacar's longevity and lives to be 235 - only three years less than his father. He also inherits the fearless spirit of his mother's people.)
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Actually actively averted in the Elves of Alfheim supplement for the Mystara campaign. Elven romantic relationships are not expected to be "for life" and it is rare that an elven couple doesn't drift apart anyway after at most a century. Elves with human spouses don't like when they die, of course, but don't see this trope as a big problem.
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Black Dagger Brotherhood: Both Mary and Jane were humans hooking up with vampires, so Mary became immortal to make up for being barren and Jane became a ghost.
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A "villain" of an episode of Class of the Titans, an immortal nymph, kidnaps Odie in one episode as she once loved Odysseus and Cronus convinces her that Odie is his reincarnation (he's actually a very distant descendant). Odie actually does reciprocate her feelings as, clinginess aside, she's incredibly kind and beautiful, but he can't stay with her yet as he still has to defeat Cronus. Hearing this she lets him go, explaining that as an immortal she literally has all the time in the world to wait for his return.
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Briefly touched on in Glory Road by Star's sadness, and a thought "If only I were a [mere] hundred years younger" than her mortal husband.
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Lisa from Beyond the Walls is a woman of around 30 years, living in the 2000s. She falls in love with Julien, who served in World War one and has been trapped in the House ever since. At the end of the story, when the House returns him back to his time, they are separated, with him writing a book about his life to her. He is well in his 70s when she is born, which he laments.
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Star Trek:
Due to the great difference between Vulcan and human lifespans, Spock's father was sure to outlive his mother by many years. (This wasn't addressed much in The Original Series.) Sarek has a different human wife, Perrin, in The Next Generation, so Amanda must have died between the generations, but we don't know when (Though the Expanded Universe novel Sarek includes her death from natural causes shortly after the events of the sixth movie).
The same issue might come up with Klingon/human relationships, as Klingons live 150 years or so. Or it might be a MFDR in the other direction, as they much prefer to die in combat while they're still young.
Worf's more prominent (and only non-Klingon... er... Half-Klingon) marriage was to a joined Trill, which confuses, and, depending on one's interpretation of the joined Trill/Symbiont relationship, laughs in the face of the whole matter. (None of the major Daxes have had any problem with long-term couplings with persons who aren't joined Trill.)
In the Star Trek: The Original Series episode, "Requiem for Methuselah", the immortal, 6,000-year-old human Flint cites the tyranny of this trope as his motivation for creating a Robot Girl mate as brilliant and immortal as himself.
Data of Star Trek: The Next Generation, being an android, doesn't age and could theoretically live forever, so any relationship he enters into (unless it's with another artifical life form) is this, although none of the relationships depicted onscreen last long enough for this to matter.
In the Star Trek: Deep Space Nine episode "Chimera", the changeling Laas brings up this trope while trying to convince Odo (a changeling whose species has an incredibly long lifespan) to leave Kira (a Bajoran with a roughly human-like lifespan) in order to join Laas in locating the rest of the Hundred.
Star Trek: Voyager had a couple of these.
For most of the first three seasons, Kes, whose race has a nine-year lifespan, was in a relationship with Neelix, whose life expectancy was apparently like humans. Kes's replacement, Seven of Nine, had her own age issue — she was only six when the Borg assimilated her, making relationships with the adult crew somewhat dubious. The exception was the Doctor, who was technically only a few years old himself. Thus Doc/Seven (teased, but never followed through on) was a rare example of a Mayfly December Romance that looked ickier than it was.
Explored also in "Before and After", in which Kes is traveling backwards in time, so we see an alternate future where Kes is married to Tom Paris while his friend Harry Kim is married to Kes's daughter.
The Doctor gets another in the final episode, "Endgame", that has scenes set in the future. He married a human woman, but then that future was changed when Janeway went into the past to get the ship home sooner.
The Star Trek: Enterprise episode "Exile" features an alien who has already loved his way through a few mayflies, and he wants Hoshi to be the next one.
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Kingdom Come: The series shows a still-youthful Superman long after Lois Lane's death, and eventually builds up a romance between him and the explicitly immortal Wonder Woman. He's still more or less in his prime, and he's spent so many decades under the yellow sun that kryptonite doesn't bother him anymore, but his hair has begun to grey at the temples. And it's not like Lois died of old age, she was murdered by The Joker.
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Tales of Kolmar: The Kantrishakrim live for two thousand years, optimally, and mate for life. When one falls in love with a human this trope is brought up; in fifty years the human will be in her dotage or dead, and plenty of Kantri spend that long meditating or in contemplation; fifty years is also about how long it takes for a Kantri to heal from a major wound, which they do while in a comatose state. Oddly, the fact that they have ready access to a kind of elixir of youth is never mentioned by either party. When the Kantri seems to be dying, the human thinks that he should have mourned over her grave for a thousand years. Instead, though, he becomes human, though he still has Kantri blood; later on her blood is changed to be like his, so if that conveys longevity neither is too likely to outlive the other.
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One vampire in Trinity Blood is urged to confess his attraction to a human, as humans grow old and die too quickly.
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Gargoyles:
When Goliath and Elisa finally hook up, it looks like it'll be this. Gargoyles age at half the rate humans do, so Goliath still has about 115-120 years left in him. A bit more mild than most examples, but still, he'll outlive her by decades. Word of God reveals Goliath will sacrifice his life for a great cause... so maybe not, after all.
Every time one of the Children of Oberon takes human form to marry (or sleep with, whatever) a human, it's like this. Anastasia and Halcyon Renard are going through this: he's elderly and terminally ill; she's a perpetually young Physical God. It's hard to say how he'd feel if he knew.
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Girl Genius:
This ends up being the romance between Zeetha and Airman Higgs, as the former is young woman in her twenties while the latter is an immortal, thousand-plus year old Jaegermonster. Except Zeetha has now been dosed with the same Super-Soldier potion, so who knows what's going to happen.
Played straight with Oggie the Jaeger and his long-dead wife; he feels she's still alive as long there are descendants around, and he makes a constant effort to see that his great-grandchildren keep procreating.
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The Better Bones AU has Fallenleaf and Cinderheart - a variation where despite Fallenleaf being a god more than 100 years old (which is extremely old by cat standards) and Cinderheart being a normal cat, they grew up together thanks to time travel shenanigans.
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Trail of Lightning: Neizghání is an immortal. Maggie is a sixteen-year-old human. They hook up, but he dumps her in her mid-twenties. One interpretation is that he's just really into teenagers.
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Invincible: Discussed when Omni-Man reveals his true background to Mark. He's an alien whose people live for thousands of years, and he claims to see Mark's mother as little more than a pet he will long outlive. This is also the underlying theme of his We Can Rule Together speech ("What will you have after 500 years?!")
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The Baxters in The Sisters Grimm: the first time they're introduced, Cinderella (an Everafter) looks like a gorgeous twenty-year-old, and her husband Tom (a human) is well into his eighties. Tom is acutely conscious of the problem and attempts to construct a time machine that would make him young again. Said time machine disrupts the structure of the universe and has to be destroyed, so instead, Cinderella chooses to age so that they wouldn't be parted.
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Journey to Chaos: Annala refuses to consider a relationship with Eric because she is immortal and he is not. "I could blink you'll be a rotting corpse". This very thing happened to her aunt, Triste. Despite all kinds of magical aid to prolong his life, Mori just heeled over one day and it drove her insane. Eric solves this problem by asking Annala's deity, who happens to fancy himself Eric's "bestest friend", to make him immortal like her. He does and Relationship Upgrade ensues.
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In the last two episodes of the first series of Being Human, vampire Mitchell runs into an old flame of his, who is now a fairly old woman. He gives her the option of becoming a vampire, which she turns down, putting him on the path to get out of his Heroic BSoD and almost Face–Heel Turn.
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Squadron Supreme: Power Princess (a pastiche of Wonder Woman) is shown caring for her septuagenarian husband, whom she married in the 1940s when she first left Utopia Isle.
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There is a lot of Sailor Moon fanfiction that deals with this concept, since only the manga says normal humans become long-lived in the future and even if they do live a long time, they still don't live as long as the senshi. One large series by author Bill K. even features two marriages within the senshi to normal men who, obviously, die way sooner than their senshi wives. Jupiter and Mercury react accordingly... and then hook up, so there's that.
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In The Apocalypse Troll by David Weber, Ludmilla Leonovna is effectively immortal thanks to the Healing Factor her symbiote grants her. So when she falls in love with a normal man, she's very aware of the fact that she'll outlive him. Then when he's mortally injured in a fight with the Big Bad, the only option is a risky Emergency Transformation via blood transfusion, injecting some of her symbiote-laden blood into him. This kills 99.99% of the people it's done to, so she wouldn't try it except for the fact that he'll be dead in five minutes if she does nothing. Since he survives, it means that this trope gets averted for them.
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In Xenoblade Chronicles 1:
The High Entia live about five times longer than the Homs do, but they have a longstanding tradition of having a Homs consort in their royal family. The same goes for the half breeds that have resulted from such unions, and you help one get together with her Homs boyfriend on a particular quest. They never really seem concerned by the differences in their longevity in either case, though.
Machina are even longer-lived than the High Entia and would be in for heartache if they had a relationship with someone from another race; one of them, Neonik, is 9892 years old. At least a few of them were alive during the events shown in the opening scene of the game, which explains how the world of the game came to be in the form it's in.
There are relationships between Nopons and other races. The Nopon Sage has an age of 9999 years. However, this is an anomaly as the next oldest Nopon is Yusa at 83 years and is considered to be elderly by other Nopon. It may be that the Nopon Sage's lifespan was altered somehow or that he is lying or perhaps his age is due to him probably being a ghost.
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Persona:
Persona 3 The protagonist (official names Minato Arisato/Makoto Yuuki/Sakuya Shiomi) to any of the romanceable girls in all the releases of P3, due to becoming the Great Seal at the end. By extension, the female protagonist (official name Kotone Shiomi, but the fandom more often calls her Minako Arisato), to any romanceable guy except Shinjiro in the PSP release.
A bit of a technicality, but in Persona 4 Golden, you can romance Marie, who is later revealed to be a goddess. While not stated in-game, this essentially means she can't die (at least, not by natural means).
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The Fifth Element, with Leelo being the December here. (Being at least a multiple of 4000 years old...)
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Yin and Yang Series:
Fujuju and Eliza.
Subverted with other inter-species relationships, as in their human form, Keronians age the same rate as regular humans.
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In Animorphs it's the case with Tobias and Rachel. Tobias is permanently trapped in the shape of a red-tailed hawk, and refuses to become human again, though he could. Rachel, on the other hand, is a human and therefore has a much longer life expectancy than he. However, it ends with Rachel being killed in combat.
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In The Wheel of Time, this trope is why Aes Sedai rarely marry: they know that they will far outlive their husbands, and probably their children.
And grandchildren. And great-grandchildren too. The will most likely die around the same time as their great-great-granchildren. The average age expectancy for a channeler who has sworn on the oath rod is somewhere between 2 and 3 centuries. For one who hasn't its somewhere around 6.
And strangely, those Aes Sedai who do end up in romances tend to be young for their profession and fall in love with men who are getting on in years. Examples include Nynaeve and Lan, Moiraine and Thom, and Siuan and Gareth Bryne. In all of these cases, the man is older than the woman anyway, but she can expect to live another two centuries at least.
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The Echo Ranger: In Chapter 17, a still-alive Karone reveals that Andros and Ashley got married, but the former outlived the latter. She explains that humans from KO-35 have an average lifespan of 260 years, and Ashley eventually passed away of old age despite ocassional trips to Aquitar for treatment.
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In Toll the Hounds another Tiste Andii, Spinnock Durav, is apprehensive that he fell in love with not only a comparatively short-lived human, but one that is barely of age at that; Salind being in her early 20s and Spinnock being thousands of years old.
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A huge concern for the fans of Kyo Kara Maoh!, a show whose main plot is ending racism between humans and a race of demons that age at a bit less than a fifth the rate. Fifteen-year-old main character Yuuri is engaged to the eighty-two-year-old Wolfram, and an interracial marriage has taken place without mention of the aging discrepancy. Addressed later in the tragic romance between Cheri and Don Hiri, but Yuuri's aging still seems to have occurred to no one (though he occasionally makes old man jokes to Wolfram in the manga). Given that Yuuri is the demon king, not only in name but in occasional Alter Ego bouts of spectacular magic, it's really not clear that he has a normal human lifespan.
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Temporal Anomaly has Sougo Tokiwa/Oma Zi-O - who is an sixty-nine year old man that looks around eighteen - becoming lovers with the Intoner sisters - who are all two years old at most despite looking and acting like young women in their very late tens, with the exception of Zero, who is and nineteen year old that looks seventeen.
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One ending in SaGa Frontier has one of these. Asellus' Half-Mystic ending has Gina, a human, shown as a grandmother while her beloved Asellus is still the young woman she was when they first met. It's becoming harder for Asellus to come back every year and see Gina grow older.
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Showa & Vampire: The heroes all have extremely expansive power packages that include eternal youth, but the thing is it's a harem romance fic, and a lot of them have lovers that don't have that advantage. So much goes on that it never has a chance to come up, though.
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Rune Factory 4 has a romance plot with Margaret, an elf, who doesn't want to fall in love with the main character because she knows she will outlive him. The knowledge that he will die well before she is even half done with her life becomes a reason she tries to turn Lest down despite actually loving him. This comes to a head during her pre-marriage event where her voice is stolen by a siren, and said Siren is looking for a man who is has not come to the lake in an extremely long time. Margaret and Lest eventually deduce that this man lived a long time ago and has died, and the Siren knew he was likely gone, but believed she would somehow bring him to her despite death with song. When Lest and Margaret open a melody bottle containing a recorded message from the man, the Siren realizes he loved her until he was too old to come to the lake, and she waited too long to tell him she loved him. As the Siren returns Margaret's voice, she tells Margaret to not become the same as her, and leaves. Margaret kisses Lest, and decides that she will not wait either. She feels it would be better to love Lest and live saddened at his passing in the future, than to deny her love and live in loneliness for the rest of her long-lived life. With the encouragement of Porcoline (her surrogate parent), she accepts Lest's offer for marriage should the player give one.
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Top 10: As the series is a satirical deconstruction of the superhero genre, a minor background action outside a courthouse turns this on its head. Two men feud over "The Immortal Woman", because they were extremely shallow, and wanted to have a trophy wife who would remain supermodel-perfect for their entire lives, and thus not need to be dumped and replaced after a few years.
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In the Star Trek: The Original Series episode, "Requiem for Methuselah", the immortal, 6,000-year-old human Flint cites the tyranny of this trope as his motivation for creating a Robot Girl mate as brilliant and immortal as himself.
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The Pony POV Series addresses this by having Present!Rarity admitting she knows of Spike's crush on her but is afraid of mentioning it for this reason, as its established Spike will outlive her under normal circumstances. Subverted in Dark World, where Rarity was made immortal by Discord, and thus a thousand years later, once Discord's control is broken, there's nothing stopping them from hooking up, which they eventually do. As an added bonus, Spike won't naturally outlive Rarity because of said immortality.
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Kubera:
This trope is discussed, as Ran recalls his mother - a half-blood sura with an extremely long lifespan - warning him not to fall in love with a pure-blooded human because in the end, he is the one who will be hurt.
Another example is the relationship between Agni, the god of fire, and Brillith, his summoner. Since Agni is effectively immortal, he knows he's setting himself up for this, and worse, keeping him summoned is only shortening Brillith's lifespan.
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Hana, the 14-year-old girl (for most of the story) of Hana to Akuma is in love with Vivi, a demon who will live centuries longer than her. Naturally, he is constantly tormented; he hates celebrating her birthday because it means she's closer to death, and frequently counts down her remaining years in panic. When he comes to return her romantic affection, he tries to leave to let her live a normal life. It's futile, though, as he can't keep away and she's more than happy to continue their relationship. They marry, and she dies at an old age, having spent their life together. It's a Bittersweet Ending though, as she left him two children who have lifespans as long as his.
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In Legends of Dune Vorian Atreides is gifted with an extended lifespan by his Cymek father, Agamemnon. Later, when he swaps sides to free humanity, he has troubles settling down into a proper relationship due to have a several century long lifespan, so ends up taking lovers on many different planets. When eventually he settles down with a woman from Caladan, she ages normally and he ages slowly, leading to him still seeming in his 20s when she is dying of old age. He attempts to make himself look older with grey hair dye, unsuccessfully. Eventually she dies, and he does not speak to his sons again due to the awkwardness of them seeming older than him. Eventually he meets a granddaughter from one of his one night stands. She appears similar in age to him.
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An early first season episode of Bewitched focused specifically on the issue, with Samantha (apparently) admitting she will still appear to be in her twenties when Darrin is in his seventies. The dilemma is solved when Samantha uses her magic to age along with Darrin. It is unclear whether this would include her actually dying with Darrin instead of living centuries after his death, but for her to shorten her lifespan so radically to age as Darrin ages would provide yet one more reason for Endora's continual efforts to turn Samantha against Darrin. (Given the fact the series ran for eight seasons, it was actually possible to see Samantha make good on her promise as the actress aged into her late 30s as the series progressed.)
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Macross Delta: Hayate and Freyja's relationship plays with this trope - they are not really that far apart (Hayate's 17, Freyja's 15 by the end of the show) in terms of age, but the fact Windermerians live only up to about 30 will inevitably make their romance this trope. This is a source of tension multiple times, especially in the final episodes where Freyja begins to display signs of crystallisation, usually only shown in Windermereans towards the end of their lifespan.
Absolute Live, the second movie, examines this trope in greater detail, with multiple characters warning Hayate of the downsides of the trope (primarily, that he will outlive Freyja by a significant amount even if she lives most of her potential lifespan which has been drastically reduced due to overuse of her Rune). In the end, Freyja dies as a result of a Heroic RRoD, leaving Hayate alone.
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The Elder Scrolls:
Any relationship between a member of the Long-Lived races of Mer (Elves) and a member of the races of Men (who have lifespans like those of real life humans) is one.
A specific example from the series' backstory is Emperor Tiber Septim, founder of the Third Tamriellic Empire, and the young Dunmeri noble Barenziah. (Which was ironically a May–December Romance in the opposite direction, as Septim was many decades Barenziah's senior.) Barenziah was being groomed to be Septim's loyal Puppet Queen in her newly vassalized homeland of Morrowind. Barenziah actually became pregnant by Septim, and since a bastard child with a Dunmer mistress would be very inconvenient for Septim, he ordered that the child be magically aborted, much to Barenziah's dismay. Being a long-lived Dunmer, Barenziah would go on to outlive Septim by centuries.
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In A Song of Ice and Fire fanfic The Widow, such is the nature of the relationship between Roose Bolton and Walda Frey, since Roose is revealed to be The Ageless half-human, half-Other who kills the son that resembles him the most and takes his skin every few decades to stay under the radar. Having found a Morality Pet in Walda, he is uncertain on how their relationship can progress after Roose Bolton's "legal" death and him taking the skin of Ramsay. In one of the work's two endings, he finds a good-hearted human husband for Walda and sends her away. In the other, though, he marries her again as Ramsay, but Walda deduces his true identity very quickly and is overjoyed he is alive; she stays by his side for three generations before dying of diabetes at seventy-five. The usually stoic Lord of the Dreadfort weeps at her funeral.
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Ojamajo Doremi: During the Mo~tto! season, it is revealed that this is the reason the Witch Queen from two reigns ago goes crazy and creates all kinds of troubles, such as cursing Hana-Chan and creating the Smiling Moon rulenote  Travel between the human world and the witch world can only be done when a smiling moon appears in the sky. Hana-chan bringing Doremi into the witch world when the smiling moon was not present prompted the former queen to curse her., the Magic Frog Cursenote  Any witch declared to be so by a human will be turned into a little green blob-like creature known as a Magic Frog., and the Cursed Forest.
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The Unexplored Summon://Blood-Sign has this for Kyousuke (human) and the White Queen (Eldritch Abomination with Complete Immortality). The former might not want this relationship, but the latter very much does, and it's uncertain how she plans on handling this issue. Early on, she makes a seemingly-flippant suggestion that she plans on making him into an immortal like her, but it hasn't been brought up since.
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In the Star Trek: New Frontier Expanded Universe series, Selar (a Vulcan with a lifespan of about 250 years) mates with a Hermat (with a 40-year lifespan...and both sets of genitals). Selar carries a child to term...and it turns out he has the lifespan of an Ocampa (10 years, if he's lucky.) In the most recent novel of the series, Treason, this gets fixed, though ironically (for multiple reasons) Selar dies before this happens. It's not a happy book.
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In Futurama's "Proposition Infinity," Bender's Robosexual relationship with Amy is shaping up to be this, although they break up by the end of the episode.
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Kamisama Kiss: This is one of the reasons Tomoe refuses to admit he has feelings for Nanami is because he is a Kitsune and well over five hundred years old by the time Nanami first meets him while Nanami is an Ordinary High-School Student.
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In Code Geass, Mao is in love with C.C., an immortal woman with the looks of an older teenager, who he's been with since he was six. His out-of-control Telepathy (which she is immune to) gives him no other options outside of her.
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The Fall of Númenor: this trope played in the marriage of Aldarion and Erendis on Númenor, lost home of the Dúnedain. Númenóreans had a lifespan about three times that of ordinary humans, but those of the royal house lived about twice as long. Aldarion was the 6th king of Númenor; Erendis his wife was not from the royal house. She was also much younger than him, but still most likely to die first. Aldarion's long lifespan and his tendency to make multi-year voyages while Erendis continued to age (relatively) rapidly drove a massive, nasty wedge in their relationship. Their problems in turn embittered their daughter, the future queen Tar-Ancalimë. Erendis dies in Second Age 985, over a century before Aldarion dies. Aldarion lived to be 398; Erendis died at only 214. She did drown herself, but she was already old aged by then. Ancalimë inherits her father's longevity and actually lives even longer than him - she dies at the age of 412.
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"Old Man" Andrew, a supporting character from Mega Man Zero had this as a part of his backstory. He was a Reploid, she was a human, when she started aging he at one point had himself converted to look old, guess the mind must've followed suit because all he does nowadays is be by himself reminiscing.
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Another Touhou Project remix that uses this heavily (in a very beautiful waltz) is "The song of a Broken Youkai who loved a human." I wonder what it could possibly be about...
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Mushoku Tensei: Jobless Reincarnation:
Rudeus as a young man marries two women of longer-lived races. When he dies of old age, both of his wives are still in the prime of their lives.
Cliff marries the long-lived elf Elinalise, though the impact of her outliving him is not explored.
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In The Confectionary Chronicles, Fenris is revealed to do a variation of this, as he occasionally leaves the essence of his godhood with his sister Hel so that he can live a life as a mortal man, Hel returning his godhood when she comes to claim him. When Gabriel first visits him in this fic, Fenris is now an old mortal whose wife died a few years ago but still enjoys his time with his adopted son and the son’s family (which includes Remus Lupin as his grandson), only returning to godhood when Odin abducts Hermione and Loki needs all of his children to help him rescue her.
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Final Fantasy:
Though no romance is confirmed, if Balthier and Fran in Final Fantasy XII are meant to be an Official Couple, then it is quite probable that they will experience this. Viera live three times as long as humes. Fran is probably at least 100. She can expect to be alive for another century or so - long after Balthier is dead.
You'd think combining this with Reincarnation Romance would remove the pitfalls of the trope, but Final Fantasy XIII-2 shows that this combination has even worse problems. Namely, that the "December" gets so sick of watching his lover die over and over again in different lives that he tries to destroy time to make it stop.
The Shiva of Final Fantasy XIV was once a mortal Elezen who fell in love with the ageless Hraesvelgr who loved her in return. Because they knew how short their time together would be, Shiva asked that Hraesvelgr devour her, so that their souls could be eternally bound together. Though reluctant, Hraesvelgr eventually granted her wish.
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The Lord of the Rings: The Rings of Power
Arondir, who is an at least 300 years old elf, and Bronwyn, a peasant woman in her thirties have a semi-secret relationship.
The human Halbrand and Galadriel, an elf literally older than the Sun have many scenes with Held Gazes between the two as they grow closer. When Halbrand proposes to Galadriel the tables are turned as he has already revealed himself to be Sauron and older than existence itself.
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Bicentennial Man: Andrew, or NDR114 model robot, serial number 583625, has an indefinite lifespan due to his positronic brain. After his first century, he meets and falls in love with Portia Charney, who is a normal human woman. Andrew takes steps to adjust his construction so that he can grow old with her.
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Avoided in the backstory of Suikoden III, where it is revealed that the Flame Champion gave up the True Fire Rune, the source of his immortality, to be with his lover Sana. Played straight with Jimba, whose half of the True Water Rune grants him immortality, and is revealed to be the father of Chris Lightfellow. Also heavily implied with Nash and the thousand-year-old vampiress Sierra; Nash makes it clear that he's married and the descriptions he gives of his wife certainly seem to describe Sierra, especially given that another character reports witnessing Nash meeting with a pale-skinned woman late at night.note Sierra isn't harmed in the slightest by sunlight, but she finds it unpleasant and is Not a Morning Person. They do have the option of turning him into a vampire and who knows, maybe they already did. At the very least, he has stated that he wouldn't mind spending an eternity as vampire with her. And he certainly doesn't seem to have aged much in the last 15 years.
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Per Long for This World, Aubrey de Grey and his wife Adelaide Carpenter. Aubrey is a gerontologist who plans to live forever, while Adelaide has "no interest in immortality."
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In Terra Agrippa Varus, an Azatoth, is in a relationship with Eve Arlia, a Varelien. The website's encyclopedia states that Vareliens live for about 700 years and Azatoth about half that.
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The Mummy: Tomb of the Dragon Emperor,: Alex and the 2,000-year-old Lin fall in love. She later gives up her immortality to help stop the Big Bad, leaving them free to pursue a normal relationship.
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In Nekojishi human Liao will likely pass on well before his spiritual suitors.
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Hatoful Boyfriend, a Dating Sim where the female human protagonist dates uplifted pigeons, brings up the lifespan differences between humans and birds a couple of times, especially during Ryouta's route where he points out that he'll die much sooner than Hiyoko and that he doesn't want her to go through the pain of losing a loved one and being left alone like he did with his mother. It's stated in Holiday Star that pigeons live longer than fifteen years in this universe, but still not nearly as long as humans do—and Ryouta has a chronic medical condition.
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Malazan Book of the Fallen:
The long-lived Tiste Andii, Korlat, and the already fairly old human, Whiskeyjack, fall in love in Memories of Ice. In fact, it's stated that Tiste Andii tend to have relationships with shorter-lived races, finding 200 years of marriage to their own kind wearisome and a bit pointless.
In Toll the Hounds another Tiste Andii, Spinnock Durav, is apprehensive that he fell in love with not only a comparatively short-lived human, but one that is barely of age at that; Salind being in her early 20s and Spinnock being thousands of years old.
Sandalath Drukorlat, yet another millennia-old Tiste Andii, falls in love with and eventually marries Withal, a middle-aged human man. Their marriage is a bit of a Masochism Tango, but in the end they really do love each other and are just worried about each other, especially considering Sandalath's sanity is a bit on the slippery slope, and also a bit apprehensive about their differences, but somehow manage to overlook the problems eventually.
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Queen's Blade: Echidna was well over 500 years old at the time she and her student, Irma, were sleeping together; with the latter being a teenager. Their relationship ended when Echidna walked out on her, though she has tried to rekindle it. But, as far as Irma's concerned, Echidna can go f*ck herself.
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Looming Gaia: Mr. Ocean, a cecaelia (octopus-like creature that can live for well over a thousand years), and Solveig, a normal human, were in a relationship for around 80 years, ending with Solveig's death of old age.
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In the Paradox Trilogy, there is the relationship between Devi and Rupert. It isn't known how long a symbiont might potentially live, but they show no signs of ageing and none have ever died of old age.
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Unusually, Yokohama Kaidashi Kikou deals with this in a fairly straightforward way: despite her obvious affection for Takahiro, Alpha avoids becoming romantically involved with him because she knows she will outlive all of her human friends. She encourages Makki to pursue him, and eventually settles down with Kokone.
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Maken-ki!: Yatsuno, aka Yamato no Orochi, was thousands of years older than Oosuo no Mikoto when they first met - in addition to having already reincarnated seven times. But she surrendered her godhood by marrying him and eventually giving birth to their two children. It was a decision that ultimately led to both their deaths.
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In Lunar: Eternal Blue, you find that the goddess Althena averts this by giving up her immortality and living out the rest of her life as Luna. A straighter, and more platonic example is Nall, who did in fact outlive his friends, and Ruby, who has to come to grips with the fact that she will do the same. Presumably this will be an issue for Lucia and Hiro as well.
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In Neverwinter Nights: Hordes of the Underdark, it's possible to start a romance with Lady Aribeth, who is actually dead and a petitioner spirit on the eighth level of Hell. Bringing her back to the Material Plane as a corporeal "sprit" means that she is left immortal in the sense of unaging, so in the prologue she outlives any player character, even an elf.
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In The Great Alicorn Hunt Luna states that she was married to a mortal stallion 500 years before her banishment, when he died she swore not to do that again, but after fifteen hundred years of not getting any she's feeling a little tense. On the plus side Shining Armor partially ascends in chapter 7 (he's immortal but his new wings are smaller than Snowflake's) so Cadence won't experience the same tragedy as her aunt.
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A dubiously canon segment of If the Emperor Had a Text-to-Speech Device reveals that Kitten was in one with Commander Shadowsun of the Tau. For context, 40 is considered old for a Tau, and at eleven thousand years old, Kitten is almost twice as old as her entire civilization (the Tau were in their Stone Age around 6000 years ago).
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Shadow and Bone: Kirigan taunts his romantic rival Mal with this possibility: as the Sun Summoner, Alina will almost surely outlive Mal by a long time, and he has the patience to wait years until Mal is old or dead and Alina's anger towards Kirigan has faded.
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In the Transformers Film Series fandom, it's been touched upon multiple times concerning the Sam/Bumblebee pairing. Rarer, but was still touched upon, in the SarixBumblebee pairing. Of course, after the revelation that she was a techno-organic, this pretty much vanished in fanfiction.
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The Heroes of Olympus: Aphrodite mentions that the immortal gods never stay long together with a human for much of this reason. Shortly after they have had a baby together, the divine parent leaves the family. However, there are sometimes exceptions. Demigods, on the other hand, can easily come together with humans because they have approximately the same life expectancy as theirs.
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Stardust features this. Mortal human man, immortal ex-star in human woman form -> dead man and still immortal star regent of their kingdom. In the movie they got around this handily by playing on the "heart of a star" thing, i.e. one who has the heart of a star will live forever. In the films they claim that Yvaine had "given" her heart to Tristan/Tristran, and therefore they will both live happily forever after.
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Played straight, averted, AND subverted in Lost Odyssey: Kaim has had dozens of wives and hundreds of children before marrying another immortal and is at the end of the game quite ready to spent the next 1000 years with her, Seth has also had numerous husbands/lovers and at least one of her children is still alive, Ming has no problem with the idea of marrying a man she can outlive by hundreds of centuries. The immortals' children have ordinary lifespans though, and it is shown that, even if they learn to live with the death of their loved one, the immortals still suffer from this, sometimes even going to the place of the death of their loved one centuries later.
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White Sheep (RWBY):
Salem has largely given up on her plans for world domination in favor of focusing on her family, but they are rather worried about her going insane with grief if she has to watch her husband and children die of old age. She is trying to find a way to give up her immortality and die with her husband. The gods release her from her curse at the end, allowing her to finally age.
A weird version with Ozma. Since he is thousands of years old, he absolutely refuses, under any circumstances, to have sexual thoughts for any woman under age twenty-five. The problem is that he's riding around in the head of fifteen year-old Oscar, who would kind of like to at least try to flirt with some of the cute girls his age. Ozma is not interested in letting him.
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In Life of Melody, Razzmatazz (a fairy) and Bon (a troll) end up raising a human child together. After a year or so together, Razz has started to consider settling down long-term... until one of his fairy colleagues chews him out for "getting attached", since a fairy's lifespan is more than twice that of a beast or a human. The revelation comes as an unpleasant wake-up call to everyone involved, particularly since it's implied that Razz never considered that he'd outlive his partner or adopted daughter (for instance, when he gives Bon an enchanted ring with enough magic stored up to last "a couple centuries, give or take"). The matter is settled when Razz turns himself into a human.
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Beren and Lúthien: Beren (human) and Lúthien (half-elf, half-angel). When Beren dies, his wife chooses to become mortal so they are always together.
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Miss Kobayashi's Dragon Maid:
Fafnir brings this up in when Tohru says she has no plans to return to their world. She doesn't have any problem with it.
Shouta's parents are also an example of this due to their Muggle–Mage Romance, since his father is established as being older than Tohru.
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In We Are the Night, vampire Charlotte acts pretty dissociated from her Sire Louise. Turns out the reason for that is that Louise sired Charlotte despite the latter being happily married to a man she loved and having a child with him. Later in the movie we see Charlotte visiting her daughter in the hospital. While Charlotte is still youthful, her daughter dies of age right in front of her eyes. Also somewhat counts for Louise, since the vampire who sired her died and left her restless and heartbroken. Finally, there's vampire protagonist Lena and her human love interest Tom. Late in the movie, Louise points out that, even in the unlikely event that Tom stays with her, he'll die within 60 years and leave Lena alone.
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Spice and Wolf: By the time the human Lawrence meets the wolf spirit Holo, Holo is already centuries old if not older. Her vast lifespan causes some angst for Holo; she knows she'll outlive Lawrence and worries about the possibility that time will wash away the memories she made with him.
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Some Fairy Tail fics love to hook up Lucy with Loke, who is an immortal Celestial Spirit. Although most fics ignore the longterm implications, some like Lion's Pride focus on the trouble of love between a human and spirit.
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This can also be a problem in Wraith: The Oblivion, particularly if the mortal in the relationship is a Fetter - because unless the wraith can resolve the relationship before the mortal dies, the wraith will be plunged into a Harrowing, a nightmarish psychodrama, with the wraith's other Fetters, and potentially their very capacity to see the living world again, at stake.
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In Offspring, Link is a Hylian while his wife Mipha is a Zora. They're both physically and socially teenagers, except that Mipha is over a century old. Link never put much thought into the lifespan differences between himself and Mipha until after their children were hatched. Link realized that when he died of old age, his children would only be at the end of their adolescence, but he doesn't mind because Mipha would still be around for them. In a twist of fate, this is subverted as Mipha is the one that dies when their kids are just a few months old. Link is put into a coma and wakes up a century later to find his triplets the same physical age as him.
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Critical Role: At the end of campaign 2, Caleb enters a romantic relationship with Essek. Caleb is a human in his early 30's, while Essek is a drow of about 120 years old, which puts him just barely into adulthood. According to Word of God, Caleb and Essek stayed together for many years, but broke up amicably and remained close friends once Caleb became too old.
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Kane Series: Basically, every woman Kane is with, particularly Sesi from "Lynortis Reprise", who is just a teen when they meet and she offers him her body as a payment. Once he tried to make one of his lovers immortal. It did not go very well.
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In Tales of the Questor, due to a botched Deal with the Devil centuries ago, Elves grow to full maturity in approximately 20 years—- then die shortly afterwords. One of the main characters is Sam, a fourteen-year-old HALF-elf, destined (unless a Deus Ex Machina intervenes) to die in her mid thirties. The reader may draw their own conclusions as to what this meant for her parents, and what it will mean for her. In addition Raconnans are supposed to have a lifespan of 250 years, and the author once stated that May December Romances are fairly common among them due to their long lifespans.
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Northern Exposure: The sexogenarian Hollis is married to the young, beautiful and vivacious Shelly. Hollis specifically sought out a much younger woman because men in his family tend to live to extreme old age and outlive their spouses by decades, leaving them lonely. In spite of their immense age gap, he still fears that he'll outlive her.
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The main pairing in The Crocodile God focuses on the Reincarnation Romance between Mirasol, a Filipino woman, and the Tagalog sea-god Haik of the title. Their relationship started out fine, but the Spanish conquest of the Philippines threw a wrench in it that's been going for centuries.
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The Warhammer 40,000 fic/meme Love Can Bloom concerns an Imperial Vindicare Assassin paired up with the Eldar Farseer Taldeer from Dawn of War. Baseline humans, even with age-retarding techniques like juvenat treatments, will only live two or three hundred years at most while Eldar typically live at least a thousand years, and Farseers can live even longer than that.
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In El Goonish Shive, elves are the offspring of humans and Immortals. Adrian Raven's father Blaike Raven had this kind of relationship with Pandora, but she had already come to terms with this and planned to "reset" herself after his passing. But then he was killed and she went off the deep end.
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Vermeil in Gold: Vermeil — a 550-year-old demoness — becomes the familiar of, and eventually falls in love with, teenage mage Alto.
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Warhammer has one. Specifically, the Vampire Count Vlad von Carstein and his beloved wife Isabella. Because this is Warhammer there is precious little angst over this as they are both bloodthirsty monsters of the old school, even before Isabella became a vampire.
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Beyond the Outer Gates Lies... A high school library?: Harry is in his mid to late forties chronological, even if he was de-aged to a teenager. And as a wizard, he can potentially live three to four centuries (if he doesn't do something stupid before that). Serafall's age is undisclosed, but she is at least 1,000 years old. And she is implied to have a life expectancy of 20,000 years, if not longer.
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Blade Runner, Assuming Deckard himself isn't also a replicant, and thus also subject to a four-year lifespan.
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Like in real life, ponies in Claro de Luna have an average lifespan of 25. Luna is an immortal alicorn that is well over 1000 years old. She ends up outliving Octavia, who dies at 26.
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In Delicious in Dungeon, it's indicated in an omake that one of the elf Canaries, Otta, was jailed for having a preference for halfings. Elves are the longest lived race, living three centuries on average, while halfings are the shortest lived race, with a lifespan about a sixth of that, so the other other elves see her dating halfings as akin to pedophilia, since an elf of comparable age would be a young child (made worse by adult halfings having naturally youthful faces and short heights). The fact she also tends to leave her partners after they hit thirty doesn't help her case, which she swears is because of extenuating circumstances.
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My Little Pony: Friendship Is Magic:
Winged Unicorn Princess Mi Amore Cadenza marries an ordinary unicorn in the Season 2 finale. Whether or not she's a Physical Goddess like her aunt is left ambiguous, but Word of God confirms she will outlive him either way. Luckily, another Word of God later went back on this.
There is also baby dragon Spike's Precocious Crush on Rarity, which has shades of this given that dragons are supposed to have lifespans tremendously longer than ponies. Adult dragons take naps longer than the lifespans of ponies.
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Doctor Who: The Doctor tends to avoid becoming too close to his companions because of this, due to what he calls "the curse of the Time Lords" — a companion could spend their whole life with him, but he couldn't spend his whole life with them (see quote), being "immortal, barring accidents".
The Third Doctor's relationship with Jo Grant had shades of this. Their relationship was never quite romantic, but he did seem awfully disappointed when she ran off and married a man she described as a younger version of him.
Worse still, according to Jo, she never stopped running, hoping she'd see the Doctor again someday.
An episode of the new series, "School Reunion", explored this issue in detail by focusing on aging ex-companion Sarah Jane Smith, while another, "The Girl in the Fireplace", gave the Doctor a poignant Mayfly-December Romance with Madame de Pompadour.
Played straight in the Doctor's relationship with Rose Tyler, which did become romantic and had a bittersweet ending.
Subverted in "Flesh and Stone", when the Doctor raises this trope as a defence to Amy's romantic overtures: "Aw, you are sweet, Doctor, but I really wasn't suggesting anything quite so long term."
Played with/zig-zagged and turned on its head in various ways in the case of his much later relationship with Clara, another human.
The usual expectation is turned on its head when they get separated for what, due to the time travel involved, were several centuries for him but barely more than half an hour for her, leading to a scenario where she very nearly sees him kick the bucket from old age.
While she shames the rest of his people into granting him an additional regeneration cycle, effectively procuring him a second chance at life, the experience of seeing generations of humans live and die before his eyes in all those centuries leads him to break it off, leading to a prolonged Anchored Ship situation.
All of this comes with the interesting side effect that he, previously youthful-looking and likely to have stayed that way for most of her life if not for said separation, wound up with the appearance of a man in his fifties, while Clara is still 27, reversing the situation one would expect to set in eventually.
Further played with to poignant effect in a later episode, where they were both under the impression that they had just reunited after 62 years apart, in which she never accepted anyone else's marriage proposals (and explicitly states that he would have been a worthy husband). Ironically, when actually forced to confront his fear of seeing her as a wizened old lady, he barely even perceived her aged appearance and was much more upset that they didn't spend these years together. Once they figure out that they are still in a dream state and free themselves from it, they take that lesson to heart, and leave hand in hand, intending to make the most of their limited time together.
Their story has an interesting Bittersweet Ending. Clara eventually dies by performing a Heroic Sacrifice and Stupid Sacrifice (both terms apply) and the Doctor does everything he can to bring her back, including taking over his home planet by banishing the old president (who, in fairness, was a President Evil), shooting an innocent man (who could fortunately regenerate) in cold blood, and almost creating a time paradox. In the end, he succeeds, and her resurrection has the bonus of making her immortal, but still able to die whenever she chooses, meaning that they could spend the rest of their lives together without either of them having to end up alone (and with the aging problem no longer an issue for her; plus, it's implied she's now indestructible too). The previous Anchored Ship is officially un-anchored briefly as Clara invites the Doctor to just fly away with her. However, they realise that they make each other willing to commit too extreme actions and the Doctor is forced to erase his own memories of Clara. But they both have long lives ahead of them and are both able to continue travelling through time and space in their own time machines, which neither of them thought they would ever be able to do again.
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The main character and narrator of The Green Mile turns out to suffer from this.
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The Non-Adventures of Wonderella: Parodied when Thor tries to make his excuse not to see Wonderella again after sleeping with her once on the basis that it wouldn't work out because of this trope because he's immortal. Wonderella was expecting something else and gets so angry she disproves his claim of immortality.
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Played straight in Avalon Code, where Mayor Georg married a human woman (who was, in fact, the granddaughter of his first love). If the male player character chooses Georg's daughter Sylphy as a love interest, it can be assumed this trope would apply to their relationship as well, albeit not in-game.
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Child of the Storm:
This is a problem of human-Asgardian relationships, since Asgardians treat '5000' as their 'three score and ten', though not an insurmountable one. However, a lot of the quiet tension in the background Jane-Thor romance is that to be with him, she'd have to sacrifice her mortal lifespan and watch everyone else fade away. Thor points this out when he's being nudged to propose, saying that it is no small thing to ask, and he is content to let her decide in her own time. Word of God is that it will also impact on a lot of Harry's decisions, noting that for love, he would - if necessary - choose a mortal life.
Another problem with the above is that without outside intervention, not all demigods inherit the Asgardian lifespan - and while Asgardians aren't that fertile, even with humans, and Thor took care to take precautions after The Hela Incident, once the precautions slipped in the 10th century and he ended up with a daughter he was completely unaware of. Torunn inherited the strength and durability, but not the lifespan, and died before he even knew she existed. A thousand years on, this clearly affects him.
By contrast, by the end of the first book he has made his peace with Lily's passing. It helps that a) she's Not Quite Dead, b) she gives him a post-mortem goodbye, c) she's a firm Shipper on Deck for him and Jane, gently saying reminding him of the "'til death do us part" aspect of the marriage vows.
This is also a problem for Wandless Wizards and Super-Soldier lineages, who are by no means immortal, but both live for centuries - about five hundred years in the latter case. In the case of the latter in particular, Alison Carter is in her early 60s and under the ageing make-up that makes her look like a well-preserved forty-something, actually hasn't physically aged since her mid-twenties. Her husband, by contrast, was entirely normal - though it's implied that he didn't die of natural causes.
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Star Trek Expanded Universe:
In the Star Trek: New Frontier Expanded Universe series, Selar (a Vulcan with a lifespan of about 250 years) mates with a Hermat (with a 40-year lifespan...and both sets of genitals). Selar carries a child to term...and it turns out he has the lifespan of an Ocampa (10 years, if he's lucky.) In the most recent novel of the series, Treason, this gets fixed, though ironically (for multiple reasons) Selar dies before this happens. It's not a happy book.
A Star Trek: The Next Generation novel, Immortal Coil dealt with this in connection with Data. Taking place not long after First Contact, the plotline includes Data's emotional realization of what he's always known intellectually — he will almost certainly outlive all of his friends on the Enterprise. And then another set, and another. The actual plot of the book assuaged these fears by introducing a league of artificially-created organisms, which Data could retire to whenever he wants. And then Nemesis happened...
In the Star Trek: The Lost Era novel The Buried Age, Jean-Luc Picard enters into a relationship with an alien known as "Ariel" (real name Giriaenn). Ariel is effectively immortal, and has been alive longer than humans have existed as a species. Her relationship with Picard was genuine while she had amnesia; when her memory returned, though, she began stringing the "innocent child" along as part of her master plan. Being as old as she is, she's an complete expert at manipulation, plus her people are naturally designed for it anyway.
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Discussed by Celestia in Just Before the Dawn.
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Discussed in Tron: Invasion (a very loose adaptation of TRON 2.0). Jet Bradley asks Mercury (a female Program) to promise never to worship him (Programs revering humans like we revere Gods), saying that humans age and die eventually. However, a Program's typical lifespan is about five or six human years to a human male's eighty, a fact that isn't lost on Mercury.
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A Court of Thorns and Roses: The High Fae all look young but are long lived. This means that there are multiple romances that fit this trope:
Feyre Archeron:
With Tamlin, who is around 500 while she's 19 when they first meet.
Also with Rhysand, who is 535 when they become romantically involved, while she is 20.
Nesta (early twenties) and Cassian, who is likewise hundreds of years old.
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In Sorcery 101, Pat became a vampire to keep his wife from being killed, and she's dead before the story begins. She actually died fairly young, but still old enough that they downplayed their romance around others to help hide Pat's vampirism. It didn't work, as Pat's Only Friend caught on to both facts.
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On The Almighty Johnsons, the entire Johnson family are reincarnations of Norse gods but only have limited godly powers and thus live a normal human life span. The one exception is Olaf, who is the god of rebirth and thus will stay young forever and cannot die of natural causes. The current generation of Johnsons are actually his grandchildren and he pretends that he is their wayward cousin. By his count he fathered 20 children so far and had to abandon them and their mothers when it became too apparent that he did not age. These days he no longer tries to have a long-lasting romantic relationship.
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Ice Fantasy: Ka Suo, an immortal and a prince of the Ice Tribe, falls in love with Li Luo, a mortal commoner.
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Baccano!: Two Gandor brothers, Keith and Berga, are married men, but the issue is never explicitly brought up in the story. It is possible that they haven't even told their wives Kate and Kalia that they are immortal.
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On Forever, Henry Morgan is an immortal who was born in 1779. He met Abigail in 1945 and they married in the mid-1950s. She knew his secret the entire time and was committed to him, but over time, she got older while he continued to look 35. By 1985, the strain of this difference and the way onlookers gaped at them became too much for her, and she left him with a letter saying she needed time to think. It turned out she had found a place in the country they could have lived together in peace for the rest of her life, but died before she had the chance to send the letter telling him.
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On Shadowhunters, Magnus is immortal and is already hundreds of years old, while Alec is in his early twenties and will live for a normal human lifespan. The possible complications are brought up in "Morning Star", with both of them concerned about what their future will hold.
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Their potential difference in lifespan has been a source of angst to Superman and Lois Lane in various incarnations. In particular, an episode of Lois & Clark focused on it, with Clark admitting he had no idea how fast he would age — if he aged at all. It was possibly resolved when Superman gave up some of his youth to rescue Jimmy from Rapid Aging and also to de-age the villain of the day into a baby, and one of the characters suggested that Superman had given up enough of his youth for it to no longer be an issue. Of course, since the show didn't run that long, we have no idea if Lois still has to worry about this...
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In Parsifal fanfiction The Good Knight and the Cursed Woman, Gurnemanz falls in love with Kundry. He is a normal human while she doesn't age due to her curse, so he meets her when he is twenty and confesses his love for her when he is fifty. Since she is cursed and regularly forced to serve Klingsor, she rejects him; she is only freed from Klingsor's magic when Gurnemanz is seventy and already frail and limping, so he is a little afraid of whether she (still looking young and beautiful) would still agree to marry him. She does agree, but both of them die within less than a month and are reunited in Heaven.
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In the second Night at the Museum movie Genki Girl, Manic Pixie Dream Girl Amelia Earhart, or rather a magical construct of the XX century aviatrix, tries actively to pursue a romance with Larry Dailey, the protagonist. Larry instead tries actively to spurn her (with little success...), knowing that the magic infusing her with life will wane at dawn, thus wanting to avert this scenario, sparing Amelia the knowledge of her overtly short "new lease" at life.
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In Andromeda, two out of the three women on the main cast were an avatar of a star (it only became apparent rather late in the series, but she was believed to be older and immortal much earlier), and a just about immortal android. This made the trope common enough.
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The premise of the fantasy novel Sirena, by Donna Jo Napoli, where the protagonist is one of the Greek Sirens who will become immortal after having sex with a human man. Falling in love with said man, however, makes the irrevocable gift a curse. In the end, Sirena and her love Philoctetes separate after ten years together, so they can each rejoin the society of their own kind. But they will never, ever forget each other.
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The Twilight Saga:
Bella is very conscious of this trope and has spent most of the first three books trying to convince her immortal vampire boyfriend, Edward (who is more than a century old stuck in the body of a teenager), to bite her to avoid this. In Breaking Dawn, she does end up turned into a vampire after her pregnancy makes her very sick and the delivery destroys her body.
This is also the fate of werewolf-human couples, because werewolves do not age while they are regularly phasing. The only solution for them to live equally with their partner is for them to stop phasing altogether.
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Children of Earth: "Day One" introduces us to Alice Jack's daughter who looks about the same age as him as she hasn't inherited his immortality.
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Battlestar Galactica (2003): Starbuck not only tries but actually succeeds in killing her unwanted Cylon suitor. He keeps coming back anyway.
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In Shall We Date?: Wizardess Heart, this happens in Leon's happy ending. Being a unicorn, he has a much longer life span than Liz. In the last scene, he is talking to his descendants, and thinking of the day he'll meet his beloved again.
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Hades: Demeter once married a worshipper of hers, a mortal farmer. As Demeter is a deity and the farmer was not, he eventually grew old and died. Demeter was left embittered by his passing, especially as their daughter eventually left her as well.
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In Beware of Chicken thousands of years ago, a man named Xiaoshi moved to a small village to escape the stress and danger of cultivator society and fell in love with a girl there named Linlin. Sadly, while he enjoyed the extremely long life of a cultivator, she never became one and he outlived her by hundreds of years despite her living to a ripe old age for a mortal.
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Averted in the John Carter of Mars books — you'd think this would apply with the protagonist falling in love with a Martian with a life span of hundreds of years, perhaps potentially forever, but Carter also becomes immortal for the same mysterious non-reason that he gets transported to Mars.
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Atlantis: The Lost Empire: Milo is twenty-something, while Kida is over 8,000 years old. However, it's pretty strongly implied that the crystal at the heart of Atlantis is responsible for Atlanteans' longevity, so anyone who stays in Atlantis will enjoy it as well, regardless of their origin.
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In the prequel The Infernal Devices, this is the fate that plagues Tessa. Like Magnus, she is an immortal warlock (well, warlock-nephilim hybrid) stuck in the body of a teenage girl. In the 1870s, she falls in love with Will and Jem, both whom are mortal shadowhunters. After Jem becomes an immortal Silent Brother, she marries Will and they start a family, but she does not grow old with him. After he dies of old age in the 1930s, she leaves the family for good, unwilling to see her children, grandchildren, and descendants die before her eyes. Seventy years later, Jem is freed from his duty and restarts his relationship with Tessa, but both know that, eventually, she will outlive him as well.
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The Sandman (1989):
The character of Hob Gadling, who was made immortal, states, while weeping next to the grave of one of his latest companions to die, "I thought we'd have longer. It never gets easier, people you love not being there anymore."
Dream's frequent though illegal romances are all of this form, since Dream as one of the Endless is as old as the universe (10 billion years for Neil Gaiman's purposes) and so even goddesses and really old witches will be outlived. Though he probably usually manages to destroy the relationship before old age becomes an issue.
Dream's brother Destruction has a similar relationship, with a goddess who only lived for a few thousand years.
The Sandman: Endless Nights: How Sol describes the love between the star Sto-Oa and his mortal lover Killalla:
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Karin has the relationship between Karin Marker and Kenta Usui. She does realize that she will outlive him, as she is a vampire and he is a human. However, after her memories of her family are erased and her First Kiss with Kenta stops her ability to produce blood, Karin now has the lifespan of a human and no longer remembers being a vampire, thus she is now capable of living her life with him normally.
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SHAZAM! Fury of the Gods: Subverted. 17 year old Freddy falls for the 6000 year old goddess Anthea and starts dating her by the end of the movie. Though his human form ages normally, he should be virtually immortal in his superhero form.
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On Hercules: The Legendary Journeys, the various gods have sexual encounters with mortals, but they otherwise avoid relationships with them. "The Green-Eyed Monster" shows Cupid falling for Psyche, which Aphrodite disapproves of. Part of that is because she's jealous of Psyche's beauty, but it's also because of this trope. Aphrodite notes she's had experience in this area and that mortals are like plums: they taste great for a while but eventually become prunes. Cupid's situation is resolved by Hercules suggesting Aphrodite give Psyche ambrosia.
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In Hometown Story, Harvey, one of the village children, has a crush on the village witch Sue, who looks teenage at best but is a couple of centuries old. Sue accepts to go on a date with him and bakes for him, hinting she might not mind getting something going once he gets a little older.
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To extremes in The Man from Earth. Main character John Oldman appears to be 35, but is actually a Cro-Magnon caveman who has lived through 14 000 years. This naturally causes difficulty in his romantic relationships, as he has to abandon each woman after a few years so that people don't catch on to his immortality. References are made to various women he has loved, including one of the films main characters, Sandra, a historian in her 30's. Another one turns out to have been the mother of one of the other main characters. It is implied that John knew this all along.
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Mercy Thompson:
Werewolves are immune to old age and disease and can live for centuries, barring injury and insanity (or even millennia: Bran and Samuel were alive when Christianity arrived in Wales around 1700 years ago) Some wolves do simply burn out after a while, or go mad and have to be put down. The werewolf Samuel Cornick has had three human wives, each of whom died of old age. Another, unnamed werewolf in Cry Wolf is shown kissing his elderly wife who was initially mistaken for his grandmother. In Hunting Grounds, Arthur chooses to have his wife assassinated by vampires rather than suffer watching her die of old age.
The Fae have this problem as well. Unlike the werewolves, many of them are truly immortal unless killed, and they have long had dalliances with humans that resulted in offspring. Unless their human lover is taken to Underhill, they'll age and die in what to the Fae is not much more than an eye-blink. And if they are taken to Underhill, they have to deal with the fact that their lover will tire of them after a few decades or centuries but they'll be forever unable to return home lest all their lost time instantly come back to them. The same options exist for any resulting half-Fae children: sometimes the kid will win the Superpower Lottery and be strong enough to be considered a true Fae, but often they get just a little bit of magic and a parent who might wonder off and forget to look in on them until they're a century or two dead.
Mercy herself, as a coyote walker in love with and eventually married to a werewolf, worries about this. Fortunately, it's eventually revealed that she's likely to have a comparable lifespan to Adam if nothing screws it up for them. (Which isn't outside the realm of possibility, given how much of a trouble magnet she is...)
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What We Do in the Shadows: In the end, Viago the 379-year old vampire gets together with a girl he pined after a long time ago. By the current time they get together, she's 90 years old and he is an immortal vampire who looks like a middle-aged man, hilariously making her the mayfly in their romance.
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In the Rivers of London series, some river gods take human partners. Oxley's wife Isis gained immortality (they met in the 18th century, when he was already several hundred years old), Lady Ty's husband didn't. Nobody really knows why, because nobody really knows what the deal is with the Rivers in the first place.
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Discussed in the Warrior Cats book Squirrelflight's Hope. Squirrelflight's mate has become a Clan leader, meaning that he was gifted with nine lives. She thinks about how this means that he'll likely long outlive her, and frets that he can always take another mate after she's gone, and wonders if the reason he's not ready to have more kits right now is because he has so much more time than her.
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The Sandman: Endless Nights: How Sol describes the love between the star Sto-Oa and his mortal lover Killalla:
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Tsukihime: Shiki actually has a greatly reduced lifespan compared to normal humans thanks to his Mystic Eyes and the strain it puts on him. On the other hand, his girlfriend, Arcueid, is a deathless Friendly Neighborhood Vampire. There is an epilogue that takes place years after Tsukihime and is presumably based on the Official Couple that shows Shiki as a Future Badass, so he has at least a few years left, but Arcueid will outlive him eventually.
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The Beauty and the Beast type relationship between Rumpelstiltskin and Belle on Once Upon a Time. He's a cursed immortal wizard who will live forever unless someone kills him and she is plain old human. He's something in the neighbourhood of 400 and she's 25-30. Due to magical shenanigans, it's been over thirty years since they met without either of them actually ageing mentally or physically. Season 7 has the ship reach its logical ending when Belle dies of old age and Rumple looks the same he did when they first met, leaving him desperate to find a way to die and reunite with her in the afterlife.
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The Fall of Gondolin: Tuor (Human) and Idril (Elf). It is rumored that Tuor supposedly became immortal.
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Highlander:
Reflected in the song "Who Wants To Live Forever" by Queen. This kind of romance is almost inevitable for the immortals in the film series, as they will naturally outlive any human love interests, and immortal-to-immortal romance is problematic too, as they are all engaged in a deadly battle royale with one another that won't end until only one is left.
Connor MacLeod's first love was a mortal woman named Heather in 16th-century Scotland. They were married for 53 years until her death by old age in 1590.note Heather's age is never stated, but judging by the actress's age in this film and Highlander: Endgame it appears she lived to her mid-seventies. And this was still only a tiny portion of Connor's own immortal lifespan.
Connor's mentor Ramirez explains in one scene that he was born in Ancient Egypt and he had married three times over his two-thousand year life, the last time to a Japanese princess named Shakiko, whose genius Ultimate Blacksmith father made his badass ivory-handled katana as a dowry gift. He swore off ever having relationships with mortal women again after the death of Shakiko, and even warns Connor against pursuing Heather to spare him the inevitable heartbreak. The way he talks about poor Shakiko even many, many centuries after her passing suggests he still misses her dearly.
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In It's Such a Beautiful Day, this trope is explored as the narrator goes into denial over the fact that Bill has just died and instead tells the story of him achieving Complete Immortality. Exaggerated as Bill's romances blend into one another to the point where all relationships lose all meaning and a large portion of Earth's population becomes his offspring.
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In Hotarubi no Mori e Hotaru's Odd Friendship with Youkai Gin ends up in romance as she grows up. And goes straight to Star-Crossed Lovers.
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The Children of the Goddess in Fire Emblem: Three Houses, like Manaketes, live for millennia, so it's assumed that Seteth or Flayn will outlive any of their possible love interests by centuries. The same may be true of Byleth, though due to their unique powers they may be able to control the rate at which they age and live a normal human lifespan.
Surprisingly, this was the opposite for Byleth's parents, with their father, a human, being over 300 years old (albeit thanks to his crest blood), and their mother, an artificial Child of the Goddess, not being expected to live past twenty.
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In The Inexplicable Adventures of Bob!, Voluptua gives this as one of several reasons she cannot pursue a relationship with Bob, yet also the reason she is reluctant to leave Earth's solar system. "If I turn my head for a moment... he'll age to dust before I can look back." Shown here.
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Eventually between Margery Daw and Keisaku Satou in Shakugan no Shana. As a Flame Haze, Margery has been around for a couple centuries, while Keisaku is a high school student. It also comes off as an Age-Gap Romance, since Margery looks like she's in her mid-twenties.
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The Harvest Moon series offers several supernatural love interests, but plays with things.
The Harvest Goddess and the Witch Princess, the Kappa from More Friends of Mineral Town, and Keira the century-old princess sleeping in the mines in the DS games are perfectly okay with marrying the player character, once the requirements are fulfilled. However, the fact that they are long-lived and will be predeceased by their spouse never comes up in conversation.
Animal Parade added the Wizard and the Harvest King, male versions of the Witch Princess and Harvest Goddess. The difference is that courting the Harvest King has him show reluctance to open to the player character, and actually marrying him leads to several of his lines driving home the fact that he's well-aware of outliving his spouse, explaining his hesitation.
Story of Seasons: Trio of Towns adds Inari, a fox-deity that the player can court. As fascinated by humans Inari proves to be, they become rather distraught upon realizing that they are falling for the player character, and that said player character is falling in love with them. Mostly because Inari, already a few centuries old, knows that they will outlive the player character, and is aware how their guardian duties would keep the two from being able to be able to live together like normal couples.
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In Purple Eyes in the Dark, Odagiri says that humans with the ability to shapeshift into beasts — like him and Rinko — end up having a much shorter lifespan than regular humans, often not managing to make it into their fourties. Rinko remembers that her mother, from whom she's inherited this ability, also died a young age, and becomes hesitant to get together with Shinya because of this knowledge. The two do end up getting together and knowing that Rinko is likely already close to dying.
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In the Myst series, Katran has, it appears, a normal life span. However, her husband Atrus is one quarter D'ni, and so he was still alive at 250. They were close in age. This is kind of subverted in another background novel, The Book of Ti'Ana- the lifespan discrepancy between the human Anna and the D'ni Aitrus is one of the reasons their marriage is opposed, yet the couple themselves are less bothered by the issue. However, thanks to the efforts of the villains, she ends up outliving him.
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Honkai: Star Rail: The Xianzhou Alliance actually has laws against this, as they were Genre Savvy enough to know what happens when a long-life species consummates with a human.
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Played with: Sara and Lottie in Str.A.In.: Strategic Armored Infantry both become Reasoners to see their brothers again, because relativistic effects (interplanetary travel means spending time near lightspeed and dealing with the attendant time dilation, since they don't have FTL travel) declares that once they return, the girls will be long dead. It doesn't work out well.
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More than a few Tangled works have tampered with the idea of the flower making Rapunzel functionally immortal. This makes her marriage to Eugene into this. Several have her Driven to Suicide, though not all succeed. One fanfic example is Prisoner Of Time.
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In At Arm's Length the three main characters are Enchanters and well into their 200s, while their mortal husbands are in their 20s.
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A point that's brought up by both Nowi and Tiki in Fire Emblem: Awakening if they form a relationship with Ricken and the player's character respectively, as both of them are Manaketes and capable of living for thousands of years. Nowi questions Ricken about whether he really wants to marry her when she'd be looking youthful as ever even when he's an old man, while Tiki states that she's aware that she'll have to part with the player long before her life ends, but promises she'll remember him forever.
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Justice League fanfiction dealing with Batman and Wonder Woman is often about this and Diana dealing with Bruce's inevitable death. It is actually not uncommon for post - Batman Beyond fics to avert this to an extent by having Diana sacrifice her immortality to give Bruce a second youth, thus allowing them both a normal human lifetime together.
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A variation of this trope appears in Dragon Ball Z; according to the ''Daizenshuu'', Saiyans have roughly the same lifespan as humans, the only difference being that they retain their youth. Vegeta and Bulma, for example, would probably die of old age around the same time, but Bulma will have aged much more visibly.
Flipped in Dragon Ball Super: Broly where Bulma is likely to live longer given she's regularly using the Dragon Balls to revert her age back down to 40.
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In The War Gods by David Weber, this can result frequently. In particular half-elves typically marry other half-elves or full elves because otherwise this trope will result, and also the children won't inherit the elven long lifespan. (A human and an elf, two half elves, or a elf and a half elf makes a half elf with a 400 year life span, while the oldest elves date to the cleft point 8,000 years ago from which all elves originate). This is also a serious issue with Wild Wizards, who have lifespans well over a thousand years, although its rare for multiple wild wizards to exist at the same time. All the other races of man (all of whom live longer than humans) can also breed with mainline humans, with the lifespan of their issue being all over the place.
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to Überwald and (hopefully) back again: Otto von Chriek, a Friendly Neighborhood Vampire will have a long ‘life’, while his human lovers William de Worde and Sacharissa Cripslock will grow old. This causes tension in their relationship.
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This is the reason given in Bluth's The Secret of NIMH as to why Jonathan Brisby never told his wife anything about NIMH; the intelligence-boosters also slowed their aging. From a mouse's perspective, Jonathan was near-immortal, and he couldn't bear to tell her that he would watch her age and die while he stayed young. In the book it's specified that the anti-aging treatments were separate, and started after the intelligence treatments. Nicodemus specifically discusses Jonathan's worries, confided to him, with Mrs. Brisby.
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Durarara!!: At only four years old, the human Shinra fell in love with the immortal dullahan Celty. After he becomes an adult, Celty comes to terms with her loving Shinra too and they become a couple, but the age issue is never really brought up.
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Star Trek: Voyager had a couple of these.
For most of the first three seasons, Kes, whose race has a nine-year lifespan, was in a relationship with Neelix, whose life expectancy was apparently like humans. Kes's replacement, Seven of Nine, had her own age issue — she was only six when the Borg assimilated her, making relationships with the adult crew somewhat dubious. The exception was the Doctor, who was technically only a few years old himself. Thus Doc/Seven (teased, but never followed through on) was a rare example of a Mayfly December Romance that looked ickier than it was.
Explored also in "Before and After", in which Kes is traveling backwards in time, so we see an alternate future where Kes is married to Tom Paris while his friend Harry Kim is married to Kes's daughter.
The Doctor gets another in the final episode, "Endgame", that has scenes set in the future. He married a human woman, but then that future was changed when Janeway went into the past to get the ship home sooner.
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ElfQuest just plain tears this up. The elves, magical immortal creatures, are the descendants of alien shapeshifters. After crash-landing on the planet with two moons, the aliens tried to survive: some by living as primitive humans, one by killing everything else, and one by turning into a wolf and becoming the ur-mother of a tribe of half-elf-half-wolf babies (a lot of which... didn't survive).
10,000 years later, the comic's main character Cutter, a direct descendant of the mortal wolf-blood line, pairs up with Leetah, a pure immortal elf. Drama ensues.
Heavily deconstructed during the second half of the main quest: another 10.000 years pass, during with most of the mortal elves decide to go into magical hibernation. One family of elves (who happen to look most like the "classical" elf of Western mythology) decide not to, and try to live a peaceful and fullfilling mortal life. The thing is — they just can't stop counting the years. Their youngest son, who was brought up by mortals in a tribe of immortals, decides that hibernation is a better alternative, because counting the years would make him go insane.
And then Winnowill, the series' main villain, discovers that her healing powers allow her to make mortal elves immortal. Against their will. And teaches Leetah, the hero's lifemate, that her own healing powers would allow her to do the same. After being kidnapped 10,000 years into the future, and believing (with good reason) that all of their friends are dead, Skywise (the hero's best friend) asks Leetah to make him immortal... only to find out several hours later that everyone they know is still alive.
At one point in the comic, Leetah is briefly — very briefly — tempted to "cleanse" Cutter in his sleep. She utterly hates herself for even thinking about it.
Eventually, Timmain (who was one of the original aliens who landed 10,000 years ago, and was already old back then, and is the direct ancestor of the entire wolfrider tribe) ends up together with Skywise, who time-skipped the long hibernation, and is charitably a three or four decades old at that point.
Aside from the main characters, there are many, many mortal/immortal pairings in ElfQuest, and even three cases of humans being adopted by elves.
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In you can only use your own, when Asriel proposes to Chara, they protest that this would be inevitable. Asriel replies that he's already thought that through, and their love is worth it.
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Could have happened in Charmed between Piper and Leo, given that witches have normal human lifespans and whitelighters are immortal, if Leo didn't choose to become human.
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Buffyverse:
Buffy's relationship with Angel was a mortal/immortal case. This didn't bother them much, until the Big Bad and then Buffy's mom brought it up just in time for the season finale. Angel ended up leaving Buffy for her own good... and the age issue in human/vampire relationships was apparently forgotten by all concerned at that point. (Although the problem certainly didn't figure in either Buffy/Spike or Angel/Cordelia.) Of course, the only reason they came up for that reason of Angel leaving Buffy was because they had to somehow get him out of Sunnydale for his spinoff show. Also, this was only part of the reason Angel left Buffy, the other, of course, being that she was his Curse Escape Clause.
It's fairly clear Buffy never intended anything other than a sexual relationship with Spike, and highly doubtful Spike would have thought of the issue at all. And Angel, by the time he started getting tentatively involved with Cordelia, was planning to become human again anyway.
Also it does come up for Buffy/Spike in the comics, when they are actually dating rather than just sleeping together. Spike tries to break it off partially because of this issue until Buffy tells him off for it and they decide to stay together.
The initial age problem was enhanced by Buffy being a high school teen; Buffy/Spike and Angel/Cordelia had slightly more adult girls. Buffy provides another variant: given probable Slayer life expectancy (a few years, cut short by violence) even an ordinary human romance could be Mayfly December, at least on average. Also, given the fact that Angel was fighting side-by-side with Buffy, his survival chances weren't much higher. It would have been entirely plausible for him to die in battle, leaving Buffy alive.
It should also be noted that by the time Angel starts getting involved with Cordelia she's part demon, and a damn powerful one at that. So, it's a high probability that she was as immortal as he was at that point. It should be noted that the life expectancy of each character, in terms of their relationship, was rarely brought up. Angel's stated reason for leaving Buffy was that his curse (making him unable to ever be truly happy with her, which obviously would put a strain on both of them) and his nature as a vampire (sterile and lethal reaction to sunlight basically rules out any kind of normal family situation) made him unable to give her the life she deserved.
Played with for Anya/Xander. They never had a Mayfly December Romance relationship, but only because Anya lost her immortality for the duration of their relationship, and got it back after they broke up. Notable in that she lost her immortality in an unrelated fight with Giles, and got it back only because she was so furious about the break up.
On the villainous side the Mayor seems to have genuinely loved his wife, staying with her as she grew old and died while he remained young, and gives a moving speech about it and how she ended up cursing him for his youth. In the same speech, he rebukes Angel for essentially chaining a vibrant young woman to a life in the shadows with him, ageless as he is, when she deserves better. Evil as he is, he's presented as being entirely correct and Angel takes this critique to heart.
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The Hero and the Crown: Luthe is a super master mage and at least 100 generations old, probably older. Aerin is 20 years old but magically powerful, and capable of being "not quite mortal" herself. They have a May–December Romance. But she's also in love with the 30 year old man who helped raise her, and he's basically mortal. So Aerin goes off to marry Tor (and co-rule her country with him) until he dies, and then go back to Luthe who'll still be around and probably still in love with her. Interestingly, even though she became "not quite mortal" during her adventures before marrying Tor, in The Blue Sword her descendants, while magically powerful, do not have significantly longer lifespans than others in the kingdom.
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In Katawa Shoujo, Hisao expects to die young from his heart condition, while none of his potential girlfriends have conditions that limit their lifespan.
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Subverted with other inter-species relationships, as in their human form, Keronians age the same rate as regular humans.
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Babylon 5: There is an interesting example of this with the relationship between John Sheridan and Delenn. Minbari already typically outlive Humans by one or two decades, and as both characters are about the same age she had expected to outlive him eventually. However, a Heroic Sacrifice to save half the galaxy shaved about forty years off his lifespan, leaving them a scant 20 years of married life. note A bit of irony is that it may in fact have been Sheridan that "outlived" Delenn as his body was never found, only a sealed empty ship that had him entering it but never exiting it. But then, Valen's body was never found either, even though he was entirely mortal. The batting record for members of the One being ascended to a higher plane are therefore 2 out of 3. Draw your own conclusions about Delenn's ultimate disposition.
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YuYu Hakusho
Yusuke is a demon by the end of the show, and Keiko is still a normal human. It's implied Yusuke's lifespan will be several centuries-long and since Keiko is still human, he'll live much longer than her.
Even Kuwabara and Yukina's relationship is that because ice maidens live for centuries and Kuwabara's just a human.
Raizen's relationship with the doctor he met in human world counts too, especially since it's the whole final season's plot. Her not dying of old age was the only surprise in ending their relationship.
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In Sailor Moon, senshi live for hundreds of years depending on version. Unless Usagi somehow gave the power to mortals, any relationship the senshi could have would end with their mate dying way earlier than they. In the manga it's stated that everyone in Crystal Tokyo becomes extremely long-lived.
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The trope was touched on in a side-story manga in the Record of Lodoss War series centering around the human Parn and elf Deedlit (Deedlit's Tale)`, but received practically no attention in the anime version of the story. However, it did get an English lyric song on the third TV series OST dedicated to it: "Evermore."
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Kagerou Project: Being a gorgon, Azami is immortal. When she realized that her husband, as a human, will die much sooner than her, she creates the Kagerou Daze in order to live with her loved ones forever. It kind of fails, though… The same goes for her daughter and granddaughter with their lovers.
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Completely ignored in Transformers, where romantic relationships between Transformers and human females are an uncommon but not completely rare occurrence. However, since Status Quo Is God, the relationships are never shown again after the initial episode and one might assume they've broken up again.
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I Dream of Jeannie: The trope applies to Major Nelson and Jeannie, once they marry. Once the continuity of the series is retconned, to indicate that Jeannie was born a djinni into a family of djinnis, it also becomes clear there are genies of various ages. One episode suggests that djinnis age slowly over thousands of years - Jeannie blinks up the minister who married her parents, who had just celebrated their 3000th anniversary.
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In Dark Parables: The Exiled Prince, this turns out to have been the fate of the Frog Prince. His first wife Ivy gave him her immortality (it's implied partially by accident). From that point on, he was doomed to outlive all his wives, and worse, turn into a frog again every time one died. By the time the Fairy Tale Detective comes along, this has happened four times, each wife dying of old age. The fifth wife is still alive, but she went home to father after an argument.
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Data of Star Trek: The Next Generation, being an android, doesn't age and could theoretically live forever, so any relationship he enters into (unless it's with another artifical life form) is this, although none of the relationships depicted onscreen last long enough for this to matter.
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The following is a list of statements referring to the current page from other pages.

 Mayfly–December Romance
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Castlevania (Franchise)
 Mayfly–December Romance
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Interracial and Interspecies Love Index
 Mayfly–December Romance
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Love Tropes
 Mayfly–December Romance
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Speculative Fiction Tropes
 Mayfly–December Romance
processingCategory2
This Index Will Live Forever
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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seeAlso
Mayfly–December Romance
 Atlantis: The Lost Empire / Disney / int_b1efb7a7
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Mayfly–December Romance
 Ah! Archfall! / Fan Fic
seeAlso
Mayfly–December Romance
 Anti-Cliché and Mary-Sue Elimination Society / Fan Fic / int_b1efb7a7
type
Mayfly–December Romance
 legolas by laura / Fan Fic / int_b1efb7a7
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Mayfly–December Romance
 MyHostageNotYours
seeAlso
Mayfly–December Romance
 Request And Receive Saga / Fan Fic / int_b1efb7a7
type
Mayfly–December Romance
 TheAssassinsArchivesGinevra
seeAlso
Mayfly–December Romance
 The Jill Gilbert Saga (Fanfic)
seeAlso
Mayfly–December Romance
 The Return to Gravity Falls / Fan Fic / int_b1efb7a7
type
Mayfly–December Romance
 The Weedverse / Fan Fic / int_b1efb7a7
type
Mayfly–December Romance
 TwelfthEquestriadInterview
seeAlso
Mayfly–December Romance
 A Diplomatic Visit (Fanfic) / int_b1efb7a7
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
 All-American Girl (Shinzakura) (Fanfic) / int_b1efb7a7
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Mayfly–December Romance
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Mayfly–December Romance
 An Arc for every season (Fanfic) / int_b1efb7a7
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
 Beyond the Outer Gates Lies... A high school library? (Fanfic) / int_b1efb7a7
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
 For a Diamond Is a Marveled Thing (Fanfic) / int_b1efb7a7
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
 My Hostage, Not Yours (Fanfic) / int_b1efb7a7
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Mayfly–December Romance
 PokemonMastersOfAzeroth
seeAlso
Mayfly–December Romance
 Sansûkh (Fanfic) / int_b1efb7a7
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Mayfly–December Romance
 Scootamom (Fanfic) / int_b1efb7a7
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Mayfly–December Romance
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Mayfly–December Romance
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type
Mayfly–December Romance
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type
Mayfly–December Romance
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type
Mayfly–December Romance
 The Echo Ranger (Fanfic) / int_b1efb7a7
type
Mayfly–December Romance
 The Great Alicorn Hunt (Fanfic) / int_b1efb7a7
type
Mayfly–December Romance
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type
Mayfly–December Romance
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type
Mayfly–December Romance
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type
Mayfly–December Romance
 The Voice and the Vessel (Fanfic) / int_b1efb7a7
type
Mayfly–December Romance
 This could be bad... (Fanfic) / int_b1efb7a7
type
Mayfly–December Romance
 To Love the Moon (Fanfic) / int_b1efb7a7
type
Mayfly–December Romance
 We're a Miracle (Fanfic) / int_b1efb7a7
type
Mayfly–December Romance
 A Dog's Purpose / int_b1efb7a7
type
Mayfly–December Romance
 Arthur and the Invisibles / int_b1efb7a7
type
Mayfly–December Romance
 Bicentennial Man / int_b1efb7a7
type
Mayfly–December Romance
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type
Mayfly–December Romance
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type
Mayfly–December Romance
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Mayfly–December Romance
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Mayfly–December Romance
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type
Mayfly–December Romance
 Eternals / int_b1efb7a7
type
Mayfly–December Romance
 Fred Claus / int_b1efb7a7
type
Mayfly–December Romance
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type
Mayfly–December Romance
 Night at the Museum / int_b1efb7a7
type
Mayfly–December Romance
 Queen of the Damned / int_b1efb7a7
type
Mayfly–December Romance
 SHAZAM! Fury of the Gods / int_b1efb7a7
type
Mayfly–December Romance
 The Fifth Element / int_b1efb7a7
type
Mayfly–December Romance
 The Man from Earth / int_b1efb7a7
type
Mayfly–December Romance
 The Mummy: Tomb of the Dragon Emperor / int_b1efb7a7
type
Mayfly–December Romance
 The Picture of Dorian Gray (1945) / int_b1efb7a7
type
Mayfly–December Romance
 The Wolverine / int_b1efb7a7
type
Mayfly–December Romance
 Thor: The Dark World / int_b1efb7a7
type
Mayfly–December Romance
 What We Do in the Shadows / int_b1efb7a7
type
Mayfly–December Romance
 Wonder Woman (2017) / int_b1efb7a7
type
Mayfly–December Romance
 Highlander (Franchise) / int_b1efb7a7
type
Mayfly–December Romance
 The Witcher (Franchise) / int_b1efb7a7
type
Mayfly–December Romance
 In the Land of Leadale / int_b1efb7a7
type
Mayfly–December Romance
 Is It Wrong to Try to Pick Up Girls in a Dungeon? / int_b1efb7a7
type
Mayfly–December Romance
 Kagerou Daze / int_b1efb7a7
type
Mayfly–December Romance
 Mushoku Tensei / int_b1efb7a7
type
Mayfly–December Romance
 Mushoku Tensei: Jobless Reincarnation / int_b1efb7a7
type
Mayfly–December Romance
 Spice and Wolf / int_b1efb7a7
type
Mayfly–December Romance
 The Ending Chronicle / int_b1efb7a7
type
Mayfly–December Romance
 Alliance/Union / int_b1efb7a7
type
Mayfly–December Romance
 Anita Blake / int_b1efb7a7
type
Mayfly–December Romance
 Arcia Chronicles / int_b1efb7a7
type
Mayfly–December Romance
 Beasts in Velvet / int_b1efb7a7
type
Mayfly–December Romance
 Beren and Lúthien / int_b1efb7a7
type
Mayfly–December Romance
 Black Dagger Brotherhood / int_b1efb7a7
type
Mayfly–December Romance
 Black Jewels / int_b1efb7a7
type
Mayfly–December Romance
 Blood Books / int_b1efb7a7
type
Mayfly–December Romance
 Bloodsucking Fiends / int_b1efb7a7
type
Mayfly–December Romance
 Bruce Coville's Book of... / int_b1efb7a7
type
Mayfly–December Romance
 Circe / int_b1efb7a7
type
Mayfly–December Romance
 Cityverse / int_b1efb7a7
type
Mayfly–December Romance
 Corum / int_b1efb7a7
type
Mayfly–December Romance
 Crest of the Stars / int_b1efb7a7
type
Mayfly–December Romance
 Cube×Cursed×Curious / int_b1efb7a7
type
Mayfly–December Romance
 Daniel Faust / int_b1efb7a7
type
Mayfly–December Romance
 Dark Heavens / int_b1efb7a7
type
Mayfly–December Romance
 Darkover / int_b1efb7a7
type
Mayfly–December Romance
 Deverry / int_b1efb7a7
type
Mayfly–December Romance
 Drachenfels / int_b1efb7a7
type
Mayfly–December Romance
 Dungeon Defense / int_b1efb7a7
type
Mayfly–December Romance
 Elantris / int_b1efb7a7
type
Mayfly–December Romance
 Evernight / int_b1efb7a7
type
Mayfly–December Romance
 Expecting Someone Taller / int_b1efb7a7
type
Mayfly–December Romance
 Fablehaven / int_b1efb7a7
type
Mayfly–December Romance
 Fallocaust / int_b1efb7a7
type
Mayfly–December Romance
 Flying Dutch / int_b1efb7a7
type
Mayfly–December Romance
 Green (2009) / int_b1efb7a7
type
Mayfly–December Romance
 In the Land of Leadale / int_b1efb7a7
type
Mayfly–December Romance
 Inheritance Cycle / int_b1efb7a7
type
Mayfly–December Romance
 Inheritance Trilogy / int_1fb373c7
type
Mayfly–December Romance
 INVADERS of the ROKUJYOUMA!? / int_b1efb7a7
type
Mayfly–December Romance
 Is It Wrong to Try to Pick Up Girls in a Dungeon? / int_b1efb7a7
type
Mayfly–December Romance
 Is This A Zombie? / int_b1efb7a7
type
Mayfly–December Romance
 Isaac Asimov's Caliban / int_b1efb7a7
type
Mayfly–December Romance
 Kagerou Daze / int_b1efb7a7
type
Mayfly–December Romance
 Kane Series / int_b1efb7a7
type
Mayfly–December Romance
 Kire / int_1fb373c7
type
Mayfly–December Romance
 Kyo Kara Maoh! / int_b1efb7a7
type
Mayfly–December Romance
 LegendsCycleI
seeAlso
Mayfly–December Romance
 Malazan Book of the Fallen / int_b1efb7a7
type
Mayfly–December Romance
 Many Waters / int_b1efb7a7
type
Mayfly–December Romance
 Maoyu / int_b1efb7a7
type
Mayfly–December Romance
 Mercy Thompson / int_b1efb7a7
type
Mayfly–December Romance
 Mithgar / int_b1efb7a7
type
Mayfly–December Romance
 Mrs. Frisby and the Rats of NIMH / int_b1efb7a7
type
Mayfly–December Romance
 Mushoku Tensei: Jobless Reincarnation / int_b1efb7a7
type
Mayfly–December Romance
 Night Huntress / int_b1efb7a7
type
Mayfly–December Romance
 Nursery Crime / int_b1efb7a7
type
Mayfly–December Romance
 Oracle of Tao / int_b1efb7a7
type
Mayfly–December Romance
 Paradox Trilogy / int_b1efb7a7
type
Mayfly–December Romance
 Peter and the Starcatchers / int_b1efb7a7
type
Mayfly–December Romance
 Robots and Empire / int_b1efb7a7
type
Mayfly–December Romance
 Ruination / int_b1efb7a7
type
Mayfly–December Romance
 Science and Sorcery / int_b1efb7a7
type
Mayfly–December Romance
 Secret Histories / int_b1efb7a7
type
Mayfly–December Romance
 Sirena / int_b1efb7a7
type
Mayfly–December Romance
 Soul Eater / int_b1efb7a7
type
Mayfly–December Romance
 Spice and Wolf / int_b1efb7a7
type
Mayfly–December Romance
 Star Trek: The Lost Era / int_b1efb7a7
type
Mayfly–December Romance
 Stardust / int_b1efb7a7
type
Mayfly–December Romance
 Sunshine / int_b1efb7a7
type
Mayfly–December Romance
 Symphony of Ages / int_b1efb7a7
type
Mayfly–December Romance
 Tairen Soul / int_b1efb7a7
type
Mayfly–December Romance
 Tales of the Pack / int_b1efb7a7
type
Mayfly–December Romance
 The Adoration of Jenna Fox / int_b1efb7a7
type
Mayfly–December Romance
 The Autobiography Of Santa Claus / int_b1efb7a7
type
Mayfly–December Romance
 The Bands of Mourning / int_b1efb7a7
type
Mayfly–December Romance
 The Bane Chronicles / int_b1efb7a7
type
Mayfly–December Romance
 The Belgariad / int_b1efb7a7
type
Mayfly–December Romance
 The Black Parade / int_b1efb7a7
type
Mayfly–December Romance
 The Bone Season Series / int_b1efb7a7
type
Mayfly–December Romance
 The Circumstances Leading to Waltraute's Marriage / int_b1efb7a7
type
Mayfly–December Romance
 The Company Novels / int_b1efb7a7
type
Mayfly–December Romance
 The Elenium / int_b1efb7a7
type
Mayfly–December Romance
 The Ending Chronicle / int_b1efb7a7
type
Mayfly–December Romance
 The Fall of Gondolin / int_b1efb7a7
type
Mayfly–December Romance
 The Fall of Númenor / int_b1efb7a7
type
Mayfly–December Romance
 The Fault in Our Stars / int_b1efb7a7
type
Mayfly–December Romance
 The Homestuck Epilogues / int_b1efb7a7
type
Mayfly–December Romance
 The Host / int_1fb373c7
type
Mayfly–December Romance
 The Host (2008) / int_1fb373c7
type
Mayfly–December Romance
 The Host (2008) / int_b1efb7a7
type
Mayfly–December Romance
 The Last Unicorn / int_b1efb7a7
type
Mayfly–December Romance
 The Last Vampire / int_b1efb7a7
type
Mayfly–December Romance
 The Lightlark Saga / int_b1efb7a7
type
Mayfly–December Romance
 The Mortal Instruments / int_b1efb7a7
type
Mayfly–December Romance
 The Rifter / int_b1efb7a7
type
Mayfly–December Romance
 The Robots of Dawn / int_b1efb7a7
type
Mayfly–December Romance
 The Shadow Over Innsmouth / int_b1efb7a7
type
Mayfly–December Romance
 The Shadowhunter Chronicles / int_b1efb7a7
type
Mayfly–December Romance
 The Silmarillion / int_b1efb7a7
type
Mayfly–December Romance
 The Twilight Saga / int_1fb373c7
type
Mayfly–December Romance
 The Two Princesses of Bamarre / int_b1efb7a7
type
Mayfly–December Romance
 The Vampire Diaries / int_b1efb7a7
type
Mayfly–December Romance
 The Vampire Files / int_b1efb7a7
type
Mayfly–December Romance
 Time Enough for Love / int_b1efb7a7
type
Mayfly–December Romance
 Tree of Aeons / int_b1efb7a7
type
Mayfly–December Romance
 Tuck Everlasting / int_b1efb7a7
type
Mayfly–December Romance
 Unfinished Tales of Númenor and Middle-earth / int_b1efb7a7
type
Mayfly–December Romance
 Uprooted / int_b1efb7a7
type
Mayfly–December Romance
 Wicked Lovely / int_b1efb7a7
type
Mayfly–December Romance
 Wintersmith / int_b1efb7a7
type
Mayfly–December Romance
 World of the Five Gods / int_b1efb7a7
type
Mayfly–December Romance
 Battlemamono
seeAlso
Mayfly–December Romance
 InfinityInc
seeAlso
Mayfly–December Romance
 JillGilbertSaga
seeAlso
Mayfly–December Romance
 MayFlyDecemberRomance
sameAs
Mayfly–December Romance
 Paranormalcy
seeAlso
Mayfly–December Romance
 Ptitlegygw9hsyv7n5
seeAlso
Mayfly–December Romance
 Ptitles8ehi15xdv34
seeAlso
Mayfly–December Romance
 TexasVampires
seeAlso
Mayfly–December Romance
 Ah! My Goddess (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Ceres, Celestial Legend (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Children of the Whales (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Clover (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Dance in the Vampire Bund (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Dusk Maiden of Amnesia (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Elemental Gelade (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Goodbye, Eri (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Hekikai no AiON (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Hyper Police (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Inari, Konkon, Koi Iroha (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Inuyasha (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Kamisama Kiss (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Linebarrels of Iron (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Mamotte Shugogetten (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Mermaid Saga (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Miss Kobayashi's Dragon Maid (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Mushishi (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Natsu no Arashi! (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Noragami (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Purple Eyes in the Dark (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Rosario + Vampire (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Sacrificial Princess & the King of Beasts (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Sengoku Youko (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Tales of Wedding Rings (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 The Ancient Magus' Bride (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 The Duke of Death and His Black Maid (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 The Elder Sister-like One (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 The Helpful Fox Senko-san (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 The Seven Deadly Sins (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Toilet-Bound Hanako-kun (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Trigun (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Tsukuyomi: Moon Phase (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Vampire Knight (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Vermeil in Gold (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 ×××HOLiC (Manga)
seeAlso
Mayfly–December Romance
 Yona of the Dawn (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 YuYu Hakusho (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 The Bride of the Water God (Manhwa) / int_b1efb7a7
type
Mayfly–December Romance
 Porter Robinson (Music) / int_b1efb7a7
type
Mayfly–December Romance
 The Kingmaker Histories (Podcast) / int_b1efb7a7
type
Mayfly–December Romance
 The Monster Hunters (Podcast) / int_b1efb7a7
type
Mayfly–December Romance
 AH.com Eternals (Roleplay) / int_b1efb7a7
type
Mayfly–December Romance
 Equestrian Legends (Roleplay) / int_b1efb7a7
type
Mayfly–December Romance
 Hogwarts Hocus (Roleplay) / int_b1efb7a7
type
Mayfly–December Romance
 Ilasgoc
seeAlso
Mayfly–December Romance
 Mefhor Canon Bloc (Roleplay) / int_b1efb7a7
type
Mayfly–December Romance
 Mudy Quest (Roleplay) / int_b1efb7a7
type
Mayfly–December Romance
 SerpentsHand
seeAlso
Mayfly–December Romance
 Trustfell 2 Trust Harder (Roleplay) / int_b1efb7a7
type
Mayfly–December Romance
 WALL•E Forum Roleplay (Roleplay) / int_b1efb7a7
type
Mayfly–December Romance
 Bewitched / int_b1efb7a7
type
Mayfly–December Romance
 Blood Ties / int_b1efb7a7
type
Mayfly–December Romance
 Blood Ties (2007) / int_b1efb7a7
type
Mayfly–December Romance
 Dans Une Galaxie Près De Chez Vous / int_b1efb7a7
type
Mayfly–December Romance
 Forever (2014) / int_b1efb7a7
type
Mayfly–December Romance
 Free Spirit (1989) / int_b1efb7a7
type
Mayfly–December Romance
 Highlander / int_b1efb7a7
type
Mayfly–December Romance
 I Dream of Jeannie / int_b1efb7a7
type
Mayfly–December Romance
 Mahou Sentai Magiranger / int_b1efb7a7
type
Mayfly–December Romance
 My Love From Another Star / int_b1efb7a7
type
Mayfly–December Romance
 New Amsterdam (2008) / int_b1efb7a7
type
Mayfly–December Romance
 Northern Exposure / int_b1efb7a7
type
Mayfly–December Romance
 Shadowhunters / int_b1efb7a7
type
Mayfly–December Romance
 Supergirl (2015) / int_b1efb7a7
type
Mayfly–December Romance
 Ultraseven / int_b1efb7a7
type
Mayfly–December Romance
 Weird Science / int_b1efb7a7
type
Mayfly–December Romance
 Bat Out of Hell (Theatre) / int_b1efb7a7
type
Mayfly–December Romance
 Tanz der Vampire (Theatre) / int_b1efb7a7
type
Mayfly–December Romance
 Ar tonelico II: Melody of Metafalica (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Ar tonelico: Melody of Elemia (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Baldur's Gate II (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Choice of the Vampire (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Dragon Quest XI (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Escape Dungeon (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Fire Emblem: The Binding Blade (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Harvest Moon: Animal Parade (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Harvest Moon: Light of Hope (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Hometown Story (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Honkai: Star Rail (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 I Was a Teenage Exocolonist (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Lost Odyssey (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Lunar: Eternal Blue (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 MapleStory (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Mass Effect (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Oracle of Tao (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Paradise Killer (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Phantastical Boundaries (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 SaGa Frontier (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Soul Nomad & the World Eaters (Video Game) / int_1fb373c7
type
Mayfly–December Romance
 Story of Seasons (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Suikoden II (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Suikoden III (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Tales of Phantasia (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 The Lord of the Rings Online (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 The Sandman (2014) (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 The Wayhaven Chronicles (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Touch Detective (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Xenoblade (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Xenoblade Chronicles 1 (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Choice of Games / Videogame / int_b1efb7a7
type
Mayfly–December Romance
 Rune Factory 3 (Video Game) / int_1fb373c7
type
Mayfly–December Romance
 The Legend of Zelda: The Wind Waker (Video Game) / int_b1efb7a7
type
Mayfly–December Romance
 Akai Ito (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Aoi Shiro (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Axanael (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Cupid Parasite (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Demonheart (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Eastern Starlight Romance (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Hatoful Boyfriend (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Havenfall Is for Lovers (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Obey Me! – One Master to Rule Them All! (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Sable's Grimoire (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Senren * Banka (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Shall We Date?: Obey Me! (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Summer Rose Court (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Time Hollow (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Tsukihime (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Yami to Boushi to Hon no Tabibito (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Diamond in the Rough (Touhou) (Web Animation) / int_b1efb7a7
type
Mayfly–December Romance
 How It Should Have Ended (Web Animation) / int_b1efb7a7
type
Mayfly–December Romance
 Grim Tales from Down Below (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Kimonos Townhouse (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Carmilla the Series (Web Video) / int_b1efb7a7
type
Mayfly–December Romance
 Critical Role: Campaign One (Web Video) / int_b1efb7a7
type
Mayfly–December Romance
 Abide in the Wind (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Brawl in the Family (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Buttersafe (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Cheating Men Must Die (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Earthsong (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Klunscomic (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Kochab (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Kubera (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Pibgorn (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Poppy O'Possum (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Touhou Nekokayou (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 TwoKinds (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Vampire Husband (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Wapsi Square (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Wayward Sons (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 XY Adventures (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance
 Archie's Weird Mysteries / int_b1efb7a7
type
Mayfly–December Romance
 Atlantis: The Lost Empire / int_b1efb7a7
type
Mayfly–December Romance
 Hotel Transylvania / int_b1efb7a7
type
Mayfly–December Romance
 Human Resources (2022) / int_b1efb7a7
type
Mayfly–December Romance
 The Last Unicorn / int_b1efb7a7
type
Mayfly–December Romance
 The Secret of NIMH / int_b1efb7a7
type
Mayfly–December Romance
 The Witcher: Nightmare of the Wolf / int_b1efb7a7
type
Mayfly–December Romance
 Casshern Sins / int_b1efb7a7
type
Mayfly–December Romance
 Plastic Memories / int_b1efb7a7
type
Mayfly–December Romance
 Str.A.In.: Strategic Armored Infantry / int_b1efb7a7
type
Mayfly–December Romance
 A Charmed Life / Fan Fic / int_b1efb7a7
type
Mayfly–December Romance
 Undocumented Features / Fan Fic / int_b1efb7a7
type
Mayfly–December Romance
 mayflydecemberromance
sameAs
Mayfly–December Romance
 Chrono Crusade (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Natsume's Book of Friends (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Nura: Rise of the Yokai Clan (Manga) / int_b1efb7a7
type
Mayfly–December Romance
 Torchwood / int_b1efb7a7
type
Mayfly–December Romance
 Wizards of Waverly Place / int_b1efb7a7
type
Mayfly–December Romance
 Amplitude (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Nekojishi (Visual Novel) / int_b1efb7a7
type
Mayfly–December Romance
 Errant Story (Webcomic) / int_b1efb7a7
type
Mayfly–December Romance