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Romantic Runner-Up

 Romantic Runner-Up
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FeatureClass
 Romantic Runner-Up
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Romantic Runner-Up
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RomanticRunnerUp
 Romantic Runner-Up
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Advertisement:propertag.cmd.push(function() { proper_display('tvtropes_mobile_ad_1'); })You know, there isn't really anything wrong with this guy. He just doesn't measure up for some reason. Somebody else can make the jokes he tells a little funnier. He could use a little help in the wardrobe department. He loses a lot of women to the taller, more handsome, more suave guys (and/or the bad-boy types). Or, maybe he has all of those qualities, yet somehow isn't quite Mister Right Enough for the leading lady, who prefers the Protagonist's flaws.
The reason this character shows up so often in stories is likely to make a statement about the mysterious ways of love and about how the chemistry between two people is something that cannot be predicted. This message is a little undercut by the fact that certain people seem to be exactly the type to be cast as second-runner in a romance. Perhaps the chemistry is not so mysterious, after all.
Advertisement:propertag.cmd.push(function() { proper_display('tvtropes_mobile_ad_2'); })Note that although this trope largely applies to male characters, it can occasionally affect female characters as well, particularly in Love Triangle relationships where there're two women and one man. In these cases, the exemplar of this trope is usually the "Betty" of a Betty and Veronica matchup.
Sometimes called "The Baxter" (but not Ted Baxter) from C.C. Baxter of The Apartment, a sad sack who actually gets the girl. The Michael Showalter movie The Baxter deconstructs the concept. Compare Hopeless Suitor, Romantic False Lead, Unrequited Tragic Maiden, and No Sparks. See also Did Not Get the Girl and Everything but the Girl when it's The Protagonist who is the romantic runner-up.
Note that since this trope involves the resolution of love triangles, SPOILERS AHEAD!
Please don't use this trope to bash Official Couples that you don't like, too.
Advertisement:propertag.cmd.push(function() { proper_display('tvtropes_mobile_ad_3'); })Examples:
 Romantic Runner-Up
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2020-11-24T15:02:46Z
 Romantic Runner-Up
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2020-11-24T15:02:46Z
 Romantic Runner-Up
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DBTropes
 Romantic Runner-Up / int_12451e5f
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(500) Days of Summer is interesting in that one of these is the main character and it is about the fact that while he was completely in love with her, she wasn't at all in love with him(which isn't a spoiler). The key theme is the difference between his expectations and the reality of the situation.
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Shouta from Momokuri is this to his best friend Rihito. Rihito has always been popular, and while Shouta's far from a bad catch, he's just not quite to the level of hot-guy Rihito. Even Shouta's Childhood Friend Yuzuki, who everyone in the entire series has described as either being in love with him or not realizing she's in love with him, winds up dumping him for Rihito in the end.
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Dr. Tomoaki Araide in Detective Conan. Dude's handsome, soft-spoken, rich,... and he happens to have a romantic interest in a young girl named Ran, who has been smitten with the Guile Hero Shinichi/Conan already for years. One of the OAV's shows what would likely happen if Shinichi never found a way to become normal... Araide would lose even then, since Ran would rather be alone than without Shinichi. Thank Gods it was All Just a Dream...
An even more blatant example is Inspector Shiratori, whose biggest in-story role was being part of the Love Triangle between Sato and Takagi. It's later explained that his reasons to like Sato go beyond the mere Love Triangle, and were centered on someone else in the end.
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The Michael Showalter film The Baxter is a parody from the perspective of one of these guys.
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Advice and Trust:
As far as it is known, Chihiro Tanaka is not a bad girl -albeit persistent and meddlesome-, but Shinji loves Asuka in spite of all her flaws.
Rei is Shinji and Asuka's friend, they would do anything for her and they would never hurt her. But when she confesses she loves them both, they are too committed to each other to consider a three-ways relationship (not that she would interfere anyway).
 Romantic Runner-Up / int_1a21786a
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Ranma ½ has one for either member of the main couple:
Akane openly considers Ryoga to be much nicer and sweeter than her Compassionate Critic and No Social Skills fiance, but she's more or less Oblivious to Love when it comes to him, and quite scared of getting accidentally killed by his hugs, as he loses control of his strength when overly emotional. That said, Ryoga does find somebody else...
Shampoo is the only girl besides his fiancee that Ranma has ever shown explicit attraction, even when she was trying to murder him, and admits she can be much nicer... Except Shampoo made a horrible first impression with the whole "trying to murder him" thing and has a very strange morality that makes her act in ways Ranma can't stand.
 Romantic Runner-Up / int_1b386512
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Dean Forester from Gilmore Girls. He may have been Rory's first-ever boyfriend, but he eventually loses her to Jess and Logan as the series progressed.
 Romantic Runner-Up / int_1e703d1f
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 Gilmore Girls
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Tom Demming from Castle is a mix of this and a Romantic False Lead, as while his arc is only a few episodes and he exists, essentially, to wake Castle the hell up, he is a genuinely good guy who really does care about Beckett and seems to make her happy.
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Zach was this to Seth in The O.C. with regards to Summer. A nice guy, son of a congressman, confident, mature, and yet just not quite what Summer really wanted. The implication when he was Put on a Bus was that he went into business with George Lucas, so maybe it all worked out in the wash.
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 The O.C.
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My Best Friend's Wedding is entirely built around Julia Robert's character fighting not to become this. She doesn't get the guy, but hooks up with Rupert Everett at the end. Awwww!
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 My Best Friend's Wedding
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Stuart McRae was a very good version of this in Road to Avonlea. It made perfect sense for Felicity to want to marry him - and for her to dump him after it turned out that Gus was still alive.
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 Road to Avonlea
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Ceres, Celestial Legend features a similar situation where Yuuhi readily accepts his romantic loss to Aya's Mysterious Protector, Tooya. In the end, however, Tooya tells him that he's dying and won't live more than two years, so he asks Yuuhi to take care of Aya and their soon-to-be-born child once he's gone.
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Fringe: Poor Lincoln Lee. Let's recap: in the original timeline red-verse, he is in unrequited love and friend-zoned with Fauxlivia. This doesn't seem to change after the Season 4 reboot of both universes. In the rebooted blue-verse, he has a flirtation going with Olivia, who seems interested. Until a handsome, snarky stranger shows up who's actually her true love from an erased timeline. To add insult to injury, her choosing to remember Peter means she won't even really remember that she and Lincoln had a mutual attraction. However, after his much cooler alternative universe-counterpart dies, he decides to cross over for good and stick to Fauxlivia. Towards the end of the last season, when Olivia crosses over one last time using her cortexiphan-induced powers, it's revealed that they married and had a son.
 Romantic Runner-Up / int_28fe1376
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Sam from Charlaine Harris's The Sookie Stackhouse Mysteries books. He's her employer, and first indicated her interest when she got into her first serious relationship with another man. They're just good friends by now.
Subverted: Sam wins.
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 The Sookie Stackhouse Mysteries
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Sam Cavanaugh of Moonlighting, whom Maddie Hayes outright admits would be perfect for her — if she weren't already madly in love with her wisecracking, strip-poker-playing, flirtatious, seemingly devil-may-care partner David Addison, with whom she has the kind of romantic and sexual chemistry frequently blamed for forest fires.
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Yuuno Scrya from Lyrical Nanoha. Nice guy, helpful, supportive; he was the one who gave Nanoha her calling but relationship-wise it just didn't go anywhere and Word of Gay states that Nanoha ended up with Fate instead.
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Subverted in Sex and the City Steve looked like he would be this for Miranda, and they even broke up for a while. But in the end, his sheer averageness was just the kind of stability she needed.
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 Sex and the City
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Eleanor of Victorian Romance Emma is a female example. There's nothing wrong with her, it's just that William had already fallen in love with someone else.
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Kentarou Nara from the anime/manga School Rumble. Oddly enough, he was originally going to be the main character of the show but was nonetheless relegated as a side character with little screen time or role in the story.
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Several characters in Harry Potter: Viktor Krum, Cho Chang, Michael Corner, Dean Thomas, Lavender Brown. And Pansy Parkinson might count considering she didn't get Draco Malfoy in the end.
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Evangelion 303: Saburo was immature, sometimes overbearing, a borderline stalker and he did many dumb things and hurt people as he tried and failed to get Kaworu back... but he was not a bad person. He was just unable to control his emotions and let the past go. He also thought he was protecting Kaworu of a heart-break by interfering between Rei and him. When he realized that was not the case he gave up.
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Matt Hardy and Daniel Bryan share the humiliation of each having lost a romantic rivalry to Kane. That's right, Kane - a socially awkward, genuinely ugly, supremely sadistic borderline Humanoid Abomination. Then again, there was a saving grace in each case in that the girl in question proved to be a total slut.
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In Supergirl (Volume 2) Philip Decker dated Linda Danvers for a while and their relationship appeared to go full steam ahead... until Linda broke up with Phil because he was keeping things from her, and shortly after she met again Dick Malverne, who she was still in love with.
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Kotori is a female example from Da Capo. Many of the characters mention that she's popular, she's a good cook, smart, and she likes spending a lot of time with Junichi. Many characters also comment that those two would be a good match for each other. But unfortunately for her, Junichi's jealous sister Nemu doesn't like him spending time with any girls but her.
Sakura is another example. She even fought with Nemu at first, but eventually gives him up at the end of the first Season.
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Inuyasha: Houjou is unbelievably and relentlessly nice to Kagome, and even though the few dates they try out are disastrous, he doesn't give up. However, his name isn't in the title, so of course he's doomed to providing lots of unnecessary medicine while she runs off to save the world with Inuyasha. Fortunately, he doesn't seem to mind much.
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Artemus Gordon ends up this way at the end of almost every first season episode of The Wild Wild West. Having helped save the day (and usually the girl) most of the time, he turns to talk to either her or Jim West and finds that the girl is now in Jim's arms. From the second season on Artie's luck gets much better.
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In Överenskommelser by Simona Ahrnstedt, both of the story's protagonists have one. Beatrice has Alexandre St Cyr D'Aubigny, and Seth has Lily Tremaine. But in the end, Alexandre and Lily hook up.
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Blythe Baxter from Littlest Pet Shop (2012) had Josh Sharp falling into her arms as he swoons with her, even though he loses her each time she leaves him, hoping to go back to her room, resulting in a major heartbreak, due to the song Keep on Loving You by The Donnas.
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Simon Lewis from The Mortal Instruments, Clary chooses Jace instead of him, although he doesn't seem too affected by it in the long run.
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 The Mortal Instruments
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Kija and Jaeha from Yona of the Dawn seem to recognize right away that they are this, and actively don't act on their slight romantic affections for protagonist Yona. She's still very fond of them, and both of them are kind and handsome, but Yona simply doesn't view them in a romantic way.
Ironically Hak, the person she does end up falling for, also believed himself to be this for years due to her longstanding crush on Su-won. Needless to say, he subverts this and becomes her Second Love.
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HERZ: Kurumi was not a bad girl per se (at least if you do not count she got Shinji hammered in order to sleep with him), but she was not Asuka. Shinji loved Asuka for her beauty, brains, bravery, and fierceness, and being the only person could understand him, and he needed her badly.
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Carefree (1938)
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On Schitt's Creek: Ted, in Season 1 and 2, is the broken-hearted runner-up when Alexis chooses Mutt. However, after Mutt and Alexis's romance burns out and Mutt is Put Ona Bus, the story takes a turn and Alexis realizes she made a mistake with Ted. When Mutt returns for an episode, he becomes the runner up as Alexis won't sleep with Mutt because she loves Ted.
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Dr. Itsuki of RahXephon, anyone? Haruka initially dated someone else before the Mu arrived, then she dated Itsuki in college. Haruka's actual true love turned out to be Ayato, and they were separated literally by time and space before Itsuki ever dated her...
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Reito of Mai Hime for Mai. Mai strongly considered him at first but ended up with Yuuichi in the end.
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Damon Salvatore from The Vampire Diaries: Both Katherine and Elena prefer and have chosen Stefan over him. Is always second best to Stefan in regards to love and romance.
 Romantic Runner-Up / int_71a2d83d
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 The Vampire Diaries
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Proteus in Sinbad: Legend of the Seven Seas.
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 Sinbad: Legend of the Seven Seas
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In Hellsister Trilogy, Brainiac 5 is handsome, intelligent and well-meaning; however, Supergirl finds she can't love him back the way he wants to be loved and ends up falling for dashing but abrasive Dev-Em instead.
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Star Trek: Deep Space Nine: This has happened to Bashir twice. Leeta dumped him for Rom, whom she marries. Later on, after Jadzia is gone, Ezri tells him that if Worf hadn't come along, Jadzia would have chosen him.
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Kiznaiver:
Of the love triangle between Sonozaki, Katsuhira, and Chidori, the end game is Sonozaki/Katsuhira, leaving Chidori as this.
Of the love triangle between Nico, Tenga, and Chidori, the end is left open over who will end up with whom, but considering that Tenga had fallen for Chidori and she started developing feelings for him after the events of the show, as well as Nico openly stating she will value their friendship over any possible romance, it's likely that Nico ends as this.
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His Girl Friday (1940)
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Given the many ways one can play their character, almost all of the series' party members can be subjected to this if Shepard decides to romance one character in either of the first two games and end up with someone else in Mass Effect 3.
 Romantic Runner-Up / int_7668653b
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He does get the girl in Superman Returns. Strangely enough, that film casts Superman as the Baxter. In the first hour, at least. In the end, he still loses, Lois pretty much states that they're done as a couple and she's going to pine for Superman, because she really loves him and he is the father to her son.
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In Mass Effect, Dr. Michel has feelings for Garrus but will lose to a female Shepard who romanced Garrus in the second game, and even if the player does not romance him, he'll end up with Tali if Shepard didn't romance her.
Given the many ways one can play their character, almost all of the series' party members can be subjected to this if Shepard decides to romance one character in either of the first two games and end up with someone else in Mass Effect 3.
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Paris, of Romeo and Juliet.
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Brian Krakow in My So-Called Life may be the ultimate Deconstruction of this trope. Especially since he gets his own runner-up in Delia Fisher, and shows you exactly what the real-life consequences of at least two tropes, and a complete and utter crushing deconstructive subversion of a third.
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Between her roles on The Office (US) and Parks and Recreation, Rashida Jones seems to be building a career on playing this character.
 Romantic Runner-Up / int_82439e64
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 The Office (US)
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Kain from Final Fantasy IV.
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Subverted in Paradise Kiss. Hiroyuki Tokumori was in a love triangle with Miwako and Arashi, ending up as the loser. He also was Yukari's first crush, but then she fell for George. In the end, though, Yukari and George break up, George goes abroad... and Yukari marries Tokumori.
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Tom in Star vs. the Forces of Evil. He spends most of seasons 3 and 4 (ie nearly half the series) as Star's boyfriend, but they break up right as final story arc begins. 5 episodes later (and less than a day in-universe), Star and Marco become a couple and remain together through the finale, even bringing about the ending via The Power of Love.
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Speaking of Trope Namer Michael Showalter, how about Coop from Wet Hot American Summer? Katie's speech to him at the end basically epitomizes this trope:
 Romantic Runner-Up / int_8b157bc2
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 Stella (US)
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Danganronpa 3: Juzo becomes this when Chisa ends up as the one the love of his life, Munakata, falls in love with.
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Glee:
Sam unfortunately ends up being this. First, Quinn cheats on him and ends up choosing Finn. Then, he briefly dates Santana until she dumps him for the bully Karofsky, not knowing that they are acting as each others' beards. Then after a long term relationship with Brittany, she dumps him and gets back together with Santana a couple months later.
Artie was this after Tina dumped him for Mike.
The Quinn/Finn/Rachel love triangle had Rachel and Quinn alternating the role of runner up. The most notable instances were in season 2. Finn and Rachel broke up, leading to him and Quinn getting back together with Rachel still pining for Finn. Then Finn dumped Quinn because he was still in love with Rachel, making her the runner up.
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Part of the rivalry between Jack and Sawyer for Kate's affections in Lost. Jack is a very good guy, skilled, likable, and an excellent surgeon. Sawyer is dangerous, charming, and mysterious as well as almost entirely unlikeable. Ben points this out to Sawyer telling him that, on the island, he's the dashing adventurous bad boy while Jack is the bland doctor. Off the island, Sawyer is a two-bit ex-con and Jack is the respected, well-educated Doctor.
Later during Season 5, Sawyer ends up forming a relationship with Juliet (who had previously realized that she was essentially a Romantic False Lead for Jack). However, the sexual tension between Sawyer and Kate remains, and Juliet continues to worry that she will be this to Kate, this time for Sawyer. In the end, Jack ends up with Kate, and Sawyer ends up Juliet.
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 Lost
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Cary Elwes's character from Liar Liar.
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 Liar Liar
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A New Hope (Danganronpa): Chiaki has feelings for Hajime, who's already very close with Mikan. In Chapter 54, she admits her feelings and says she doesn't mind being "Player 3" if she has to. It's ultimately Subverted when Hajime assures he it won't come to that; he loves her just as much as Mikan. Ultimately, the three of them end up together.
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This is part of Demandred's backstory in The Wheel of Time, and is apparently why he ended up as a mass-murdering evil general.
In particular, it's massive RPT MASSIVE resentment of his status as second fiddle to the Dragon. Almost as smart, powerful, handsome, etc, etc. IIRC, he wound up playing for the side of evil so he could finally be superior.
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Cardcaptor Sakura:
Sakura and Syaoran are both in love with Yukito at the start of the story, but Yukito ends the story with Sakura's brother, Touya. At this point, it can be considered a subversion, since Sakura realized she had no romantic interest in Yukito a bit prior to their relationship started and Syaoran fell for Sakura after they captured all Clow Cards.
Tomoyo is in love with Sakura, but she much prefers the Better as Friends and I Want My Beloved to Be Happy approaches, and is, towards the end, happy to help Sakura and Syaoran get together.
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Cooper from Ben 10. In Alien Force he shows himself as a caring, humble, and really intelligent kid who has a deep crush on Gwen. However, she never showed any interest in him (she even tried to avoid him many times) and always chose Kevin over him every time he appeared. This trope was taken to the extreme in Ultimate Alien during the first season finale. Cooper had a fast growth and became a big teenager who was pretty much a palette swap of Kevin (only blonde). He worked hard to make sure Gwen's plan of stopping Kevin was a success and even defended her when Kevin almost killed her, yet all he got in the end was a thank you and a kiss on the cheek from Gwen, followed by seeing her giving Kevin a big kiss on the lips.
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The Awful Truth (1937)
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X-Men 1970: Angel is handsome, chivalrous, good-natured and rich. He believed he had a very good chance to win Jean Grey's heart until he realized she loved their neurotic, shy teammate Cyclops. Then Warren decided Scott and Jean were meant to be together and stepped out of the way voluntarily.
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 X-Men 1970 (Fanfic)
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In the anime for CLANNAD, every girl not named Nagisa falls into this trope. If it wasn't already blatantly obvious to viewers from the very beginning of episode 1, a massive Ship Sinking scene occurs in episode 18, which makes it very clear to all of the other girls which one of them Tomoya really cares about.
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Deconstructed in Rosario + Vampire with Kurumu (a succubus). It's fairly clear how heartbreaking it is for her to not be the girl to get Tsukune. It gets worse because in this universe, Unrequited Love is a bad thing for a succubus.
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Sleepless in Seattle: Nothing is really wrong with Walter and Victoria. That they are perfectly decent human beings makes you feel a little sorry for them.
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Plan B subverts this trope with Pablo. Bruno mockingly calls Pablo a "nice guy" after seeing him dating his ex-girlfriend Laura and when he asks Laura after seducing her back into bed with him if she loves Pablo, she just says that he isn't crazy like Bruno is which implies that she's with Pablo more because he's a 'safer' choice than because she truly loves him. All of this seems to be setting up Pablo as the blander Romantic False Lead who'll ultimately lose out to Bruno for Laura's affections... except that when Bruno befriends Pablo as part of a Relationship Sabotage plan, he learns that Pablo is far from a boring person to talk to and is very easy to like. So easy to like, in fact, that Bruno ends up falling more deeply in love with Pablo than he ever was with Laura and gives up on his initial plan to win Laura back in favor of hooking up with Pablo, thus making this probably the only example of this trope where the apparent Romantic Runner-Up not only wins, but does so by winning the heart of his romantic rival.
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This page describes the entire existence of James Norrington from Pirates of the Caribbean — even though he is played by Jack Davenport, he cannot compete with Will or Jack. Even in Dead Man's Chest, when he was dirty, drunk, and hot as hell. Poor fellow.
Technically Jack Sparrow too, as he also loses Elizabeth to Will in the third film. This is less tragic though because while Norrington genuinely loved Elizabeth and eventually made a Heroic Sacrifice to save her from Davy Jones, Jack's relationship with her was more Played for Laughs and he ended up getting a new love interest in the fourth film anyway.
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Julian in Something's Gotta Give. Diane Keaton dumps the much-younger, suave doctor Keanu Reeves for Jack Nicholson. Sad Keanu, indeed.
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 Something's Gotta Give
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Doctor Who:
Mickey Smith is decent, okay-looking, just an average guy with a hot girlfriend...until some guy with a leather jacket and a nice ride sweeps her off her feet.
Zigzagged between Martha Jones and the Tenth Doctor. Gorgeous, funny, extremely intelligent, and brave, Martha falls in love with the Doctor almost immediately. Which the Doctor realizes - it's just that he still misses and loves Rose. No wonder Mickey and Martha end up married.
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Jacob Black of Twilight. Specifically in New Moon when he was still nice to Bella till she showed he would choose Edward over him, after that he started to get all Alpha Male on her trying to get her grounded, kissing her by force and later by emotional blackmail. In the end, he managed to get Bella to admit she loved him, but she still loved Edward more.
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In Punch an' Pie, Heather's mother describes Heather's ex-boyfriend as squarely fitting into this trope (he hasn't been seen, though). Angela's ex-boyfriend from the prequel had a lot of these traits but doesn't quite fit the trope.
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Mako. While he did fumble up his relationships with Korra and Asami a lot over the first two seasons, one could argue that in Book Four, he was mature enough to finally hold a relationship. In the end, however, he ends up as a good friend to both Korra AND Asami. He's also the runner-up to both as the two, in the Grand Finale, have a Relationship Upgrade.
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Cupid from Ever After High seems to be headed this way. Dexter is oblivious to her crush on him, probably because he's too head over heels for Raven to notice. Raven reciprocates the feelings, and while they aren't official yet, all signs seem to be pointing in that direction.
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The Hunger Games: Sorry Gale...
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Billy Keikeya on Battlestar Galactica.
For that matter, Apollo as well. Sure, he steals Dualla from Billy but then it turns out he really wanted to be with Starbuck, who instead goes for handsome, kind-hearted jock Anders. He eventually tries to get over her but it doesn't work and he gets separated. But Starbuck's dead by that point, or at least appears to be, and things get way hectic when she comes back. Then Anders is revealed as a Cylon, but the revelation doesn't break Starbuck and Anders up as one might predict. And then, Dualla shoots herself. To top it all off, when Anders dies, Starbuck, who's Not Quite Dead, disappears again. Sucks to be Apollo.
Which is hilarious because in some ways Anders also fits. While, yes, he does actually get to marry Starbuck, it's implied a number of times that she would rather be with Apollo (and Anders knows this). At one point, she basically out-right states that the only reason she hasn't left Anders for Apollo is that she doesn't believe in divorce.
In the original series, Athena seems to be this for Starbuck.
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Misty from Vandread falls into this trope. She never really had a chance since she was introduced in Season 2, and her romantic rival, Dita, was a part of the ship's crew, and they didn't want to see her miserable (nor did she want to ostracize them any further). so she painfully gave up pursuing Hibiki, and while she tries to play off her pursuit of him as "being bored", she later goes to the park alone to cry.
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An odd example is Kyougo Monou from X1999. He did get to marry the girl he loved, Saya, and even had two children with her (Fuma and Kotori)... but he remained as the Romantic Runner Up since he knew Saya loved him but not that way, as she was in love with her best friend Tohru and married Kyougo mostly to fulfill her destiny.
Ceres, Celestial Legend features a similar situation where Yuuhi readily accepts his romantic loss to Aya's Mysterious Protector, Tooya. In the end, however, Tooya tells him that he's dying and won't live more than two years, so he asks Yuuhi to take care of Aya and their soon-to-be-born child once he's gone.
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In Corsair, Aura, a plucky (if naive) girl had been planning to marry Canale for a very long time. Though Canale really respects and cares for her he does not want to pursue a relationship for reasons even other than the obvious, and he ends up with the jerkass Bastard Boyfriend instead, who is something of an adopted sibling to Aura, just to rub it in.
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Actor James Marsden has quite the Baxter career going, playing blandly nice guys who fail to get the girl one way or another in Superman Returns, X-Men Film Series, Enchanted, The Notebook...
He does get the girl in Superman Returns. Strangely enough, that film casts Superman as the Baxter. In the first hour, at least. In the end, he still loses, Lois pretty much states that they're done as a couple and she's going to pine for Superman, because she really loves him and he is the father to her son.
And he gets a girl in Enchanted too — just not the one he was originally looking for.
And in 27 Dresses, but he's more of a Deadpan Snarker there.
And in X-Men, where Jean even marries him. Suck on that, Wolverine!
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Erfworld has Jillian, who has three people in love with her. After she leaves two behind to go after the third, one of them asks the other why he didn't go with her.
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Ashfur in Warrior Cats, when Squirrelflight passes him over in favor of Brambleclaw. This does not bode well for his mental health...
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The Legend of Korra:
Mako. While he did fumble up his relationships with Korra and Asami a lot over the first two seasons, one could argue that in Book Four, he was mature enough to finally hold a relationship. In the end, however, he ends up as a good friend to both Korra AND Asami. He's also the runner-up to both as the two, in the Grand Finale, have a Relationship Upgrade.
For some delicious irony Korra and Asami are able to bond and become closer over their shared bad experiences with dating Mako.
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Buffy the Vampire Slayer:
Xander qualifies for this trope on multiple occasions. Buffy rejects him for the more romantic Angel. Cordelia ultimately also winds up with Angel after breaking up with him. Willow, after pining after him for the first two seasons, ultimately chooses Oz over him. Even Anya sleeps with Spike after breaking up with Xander. Inverted when Buffy does begin to develop romantic feelings for Xander — and Xander rejects her for her little sister, Dawn (who had a crush on him and he rejected her).
Spike. And on a century-plus streak going at it, despite numerous metamorphoses, whether he be human, rabid young vampire, sarcastic and surprisingly sane old vampire, chipped reluctantly-good vampire, soulful good vampire, soulful bad vampire, or all-out champion of good. The irony being that most of the time he's losing out to Angel or Angelus, probably because while Angel was taking levels in badass he was getting hit by Badass Decay so hard the trope had his name for a while. Finally averted in the season 10 comics, where he and Buffy start dating, and even the brief appearance of Angel couldn't break them apart.
Riley Finn, who loved Buffy, but she didn't love him back. The interesting thing is that Riley is otherwise more the Prince Charming type. The problem is that Buffy is... well, take your pick: a) just interested in him because he's the 'normal' guy, b) not Angel.
Willow suffered from this, too, as she had a crush on Xander during Seasons 1 and 2, only for it to go unrequited, as he was more focused on Buffy and Cordelia at this point. It was only during Season 3 that they expressed mutual attraction for each other.
Oz lost out on Willow's affections to Tara in "New Moon Rising".
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Joy Mercer on House of Anubis so very much. It gets to the point where even when Nina was gone, Fabian refused to date Joy, as he believes they should be just good friends and nothing else.
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A Crown of Stars: Rei to Shinji. She is not a bad person and she cares about him, but Shinji loves Asuka, not her. Unfortunately she is too jealous to realize and understand Asuka loves Shinji back, and her jealousy is creating troubles right when they need her help.
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How I Met Your Mother:
The show deconstructs this trope in the episode "Shelter Island". Ted sees himself as the Dogged Nice Guy, and even invites fiancee Stella's Jerkass ex-boyfriend Tony to their wedding. Only when she leaves him at the altar does he realizes that Tony was actually the romantic lead of that particular love story, while Ted is the Romantic Runner-Up.
When Tony later writes and sells a movie script based on the events, Ted is pissed off and humiliated because he doesn't even get this characterization in the movie. Instead, the character based on him is an outright villain who goes around kicking dogs and doesn't even care about the female lead; he just wants to keep her away from her soul mate for laughs. The worst part is that the character, Jed Mosely, even refers to himself using Ted's real name during a Jerkass "Do you know who I am?!" rant.
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In the SHUFFLE! anime, every girl, especially Kaede becomes this once Rin chooses one near the end.
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Lancelot from Merlin has such low self-esteem that on realizing that Arthur is in love with Guinevere, gives up on his own romantic hopes without a fight or even checking with Guinevere herself to see what man she preferred (and at that point, he would have almost certainly been her first pick).
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Given a twist in the final season of Frasier in which Frasier is the bland nice guy who gets the girl while the more exciting boyfriend doesn't. Aspects of this trope are played straight by the boyfriend Frank, who is overall an extremely nice and friendly guy and a committed environmentalist.
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Friends:
David, Phoebe's on-and-off boyfriend, showed up once again in season nine and proposed. Phoebe promptly rejected him for Mike Hannigan, whom she ultimately married. To add insult to injury, the writers went out of their way to point out that the inoffensive David was a penniless failure by this point.
Also in the Season 6 finale, Richard for Monica, when she picks Chandler over him. This is rather ironic as Richard in-universe is considered the perfect guy and an Always Someone Better to Chandler. However the writers make it very clear that Monica moved on from him and it's Chandler, with all his neuroses and insecurities, who is the love of her life.
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Harvey Kinkle in the later seasons of Sabrina the Teenage Witch. After he himself dumped Sabrina after finding out she is a witch at the beginning of season 5, he kept returning to appear in the show throughout seasons 5 to 7 and kept dropping hints that he still was in love with Sabrina. But only in the very end, he gets the girl back.
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Zack Allan in Babylon 5 with regards to Lyta Alexander.
Even more heartbreaking is Lennier with regards to Delenn. They both think the world of each other, but Lennier gets Overshadowed by Awesome in the form of Sheridan. This ends horrifically when Sheridan gets trapped in a life-threatening situation and Lennier has his first "blink at the Abyss" moment in his entire life and leaves him to die. He turns back within seconds, but Sheridan is rescued by that time, leaving him with having just tried to assassinate the president of the Interstellar Alliance. He steals a fighter and flees a very confused Sheridan, who returns to Delenn to find a note from Lennier confessing the whole thing. Delenn - who never realized Lennier was in love with her - forgives him instantly, Sheridan is implied to get over it within the next day or so, but Lennier 'never forgives himself for that moment of weakness.
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