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More Experienced Chases the Innocent

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A common dynamic in the romance genre is when a character with plenty of sexual or romantic experience is paired with a character who is lacking in those departments. Depending on how the more experienced got to be that way (as The Casanova, a Chivalrous Pervert, The Vamp, a Serial Romeo, or simply having been around for longer), the relationship can play out in a variety of different ways.
For example, the experienced party may be attracted to the innocent one because their typical charms aren't working. Just as often, however, they are simply attracted to the bashful, flustered, and awkward responses to their flirtatious advances. An experienced suitor will often act as The Tease or The Gadfly to evoke reactions from the innocent which they see as a refreshing change of pace from the more straightforward dynamics that occur between equal pairings.
In some cases, the innocent character views the experienced one as an Abhorrent Admirer, especially if they are Sour Prudes and the more experienced one Really Gets Around. In other cases, the innocent is receptive to the advances and is actually grateful for their suitor's proactive behavior, but simply doesn't know how to respond. More often than not, teaching the more innocent one the ways of romance, dating, and/or sex (which they likely know little to nothing about) is a recurring plot point for this Unequal Pairing. There may also be Belligerent Sexual Tension, driven by the experienced struggling to hold back their desires for the more innocent one or actively seducing them and being rebuffed.
As with many tropes related to Nature Adores a Virgin,note The more innocent character doesn't have to be a virgin for this trope to apply this trope has its fair share of Unfortunate Implications regarding My Girl Is Not a Slut and Madonna-Whore Complex. In addition, another character may protest the relationship because of the potential power imbalance due to the difference in experience or even intervene to "protect" the virtue of the more innocent character.
In male/female pairings, women are far more likely to be the innocent party because All Men Are Perverts, All Women Are Prudes, A Man Is Always Eager, and Females Are More Innocent. When men are the more innocent one, they are likely to be shown having to overcome feelings of inadequacy because of those same stereotypes. Male innocents are almost always the case when girls Give Geeks a Chance as Nerds Are Naïve and in the Boys' Love Genre, the Uke is typically the innocent one.
It's rare for The Ingenue and the Naïve Everygirl to not be in this kind of relationship. And should the often male Chaste Hero ever figure the whole love thing out, they also frequently end up in such a relationship. Also often used alongside All Girls Want Bad Boys, I Can't Believe a Guy Like You Would Notice Me, and the numerous related tropes of Age-Gap Romance.
Compare and contrast My Girl Is a Slut and Single Girl Seeks Most Popular Guy. Related to Has a Type. See also Ladykiller in Love and Reformed Rake, which tend to follow this trope. Can overlap with Honey Pot. Not to be confused with Rookie Male, Experienced Female, which has nothing to do with romance or sex.
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In the Clear Moonlit Dusk: Because of her Bifauxnen looks and behavior, Yoi has zero experience with men, who often mistake her for a really, pretty boy. The gap between her public image and her much more innocent and chaste personality is part of what attracted the school's playboy, Ichimura, to her. He pursues her, at first casually, then more seriously which flusters Yoi. This is later lampshaded by Yoi's friend in chapter 4 who asks her, "isn't it better for a late-bloomer and beginner in love like you to be wooed strongly by a master of love?"
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Dangerous Liaisons features The Casanova Valmont trying to seduce Church Lady Tourvel as part of The Bet.
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In Heralds of Valdemar's Vows and Honor books, the maybe in her thirties Kethry clicks with Jadrek, who's well into middle age but due to his chronic pain has had almost no experience and is possibly a virgin. Kethry has had her share of lovers and convinces him that she doesn't care if he doesn't know how to please her, she'll teach him. Privately she does take a moment to rage at all the women who haven't slept with him and given him more confidence.
The Last Herald-Mage Trilogy has a Reincarnation Romance between thirtysomething Vanyel, who survived the death of his beloved as a teen, and the seventeen year old reincarnation of said beloved. Because Vanyel is Famed In-Story and it's Lonely at the Top he's been all but celibate in the meantime, but Stefan has had a very colorful last few years and on meeting Van immediately becomes a gay Ladykiller in Love, who worries that his experience repels the very pure Van. It does not. Stefan's able to leverage his greater experience to convince Van that it's not an Unequal Pairing where a powerful older man seduces a younger one. He knows what he wants, and he's pursuing it.
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In The Mister, Maxim is extremely promiscuous and develops feelings for Alessia, who is a virgin, has never been in a serious relationship and had quite a sheltered upbringing. She was kidnapped by sex traffickers and was aware of their intentions, but fled before anything worse happened. Maxim is drawn to Alessia's innocence and finds it endearing when she's flustered around him due to her inexperience.
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Bloodlines stars the uptight, inexperienced, and book-smart human girl Sydney and her developing romance with the rebellious party boy vampire Adrian. Adrian's known womanizing ways do cause friction early on in their relationship, as Sydney briefly considers that she may just be another notch on his bedpost. Notably, however, it's not this trope that attracts them to each other, but rather the parts of themselves that they hide from the rest of the world.
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Hidoku Shinaide: All 3 of the main couples in the story qualify.
Nemugasa is a Stereotypical Nerd who likes to study and do well in school. Because of this, he has zero experience with dating or sex before Maya forces himself on him. Maya on the other hand is discussed as having many previous romantic partners and is often seen being hit on by his female classmates. The majority of their early relationship is all about how Nemugasa sees Maya as an Abhorrent Admirer that's blackmailing him into a physical relationship, whereas Maya is genuinely interested in Nemugasa.
Despite sleeping with Naoya once before, Akira also has very little experience with sex and dating, having most of his previous experience in an unrequited crush on a teacher in high school. Naoya on the other hand is characterized as a guy who has been around the block a few times. This is even why Akira picked him to have Sex for Solace with after being rejected by his teacher. When the two start hooking up regularly, it's the more experienced Naoya who wants to get serious and Ice Queen Akira who is standoffish and evasive. When Akira finally reciprocates, Naoya makes it clear to Akira that up until now, he's been taking it easy on Akira to not scare him off. Now that Akira's admitted his feelings for him, he doesn't plan on holding back anymore.
Okino and Kutani are an Age-Gap Romance, with Kutani being somewhere in his late 20s/early 30s and Okino being a college freshman. They go through an Unrequited Love Switcheroo, with Kutani first asking and being turned down by Okino and then Okino pursuing Kutani, who gently tells him they should get to know each other better first. When they do eventually start dating, it's revealed that Okino has never even had his first kiss let alone done anything even remotely sexual. Kutani, having been in several relationships, takes things slow, though right after Their First Time, he reveals just how much more experienced he is than Okino by letting him know that he doesn't have a preference for what role he plays in the bedroom, much to Okino's shock.
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Some Like It Hot: Joe, in the guise of a millionaire, insists that he never felt any romantic or sexual desires after the death of his Lost Lenore, and Sugar, feeling herself as the more experienced one, decides to cure him with her kisses. Subverted, however, as Joe is as experienced as her.
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In The Ship Who... Sang, Niall falls for Helva in a serious way and tends to call her a tin-plated virgin when annoyed with her. This is some cause for concern - he Really Gets Around, and they Can't Have Sex, Ever because if he tried to crack open her life support capsule to touch her stunted human body, which he does fantasize about, he would kill her, but she's also jealous of his affairs with "softshell" women. Theirs is something of a Sexless Marriage, as she refuses to use a Remote Body.
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Arifureta: From Commonplace to World's Strongest: Yue rather forcefully seduces Hajime in the bath while they're recovering from their ordeal in the Great Orcus Labyrinth, having fallen in love with him after he freed her from imprisonment. While both are virgins, Yue was trained in the sexual arts by her aristocratic family, whereas Hajime was an introverted and socially awkward high school student prior to being Trapped in Another World.
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Grey's Anatomy: Mark Sloan, also known as "McSteamy", is an infamous playboy, whose sexual appetite becomes such an issue that the nurses at Seattle Grace unionize in protest. Lexie Grey on the other hand is The Ingenue: upbeat, highly intelligent, and idealistic to the point of naivete at times. While she has dated in the past, she's mostly depicted as a Smitten Teenage Girl for George up until now. When Mark shows interest in Lexi, everyone tells him to back off, and he begrudgingly does...until Lexi goes to his apartment, strips in front of him, and asks him to teach her. Mark relents and the two start seeing each other soon after, eventually falling in love.
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Mars: Rei is the Big Man on Campus, a Chivalrous Pervert to his female classmates and a general playboy who goes from one sex friend to the other with little care. Kira on the other hand is a Shrinking Violet who is treated as the Creepy Loner Girl because of her blatant aversion to men. She has never dated someone before. While Rei pursues Kira at first more out of curiosity than genuine romantic interest, that slowly changes over time as do Kira's feelings towards him. This dynamic is later complicated with the reveal of Kira's extensive history of sexual abuse at the hands of her stepfather. The trauma she suffers has bred a deep-rooted cynicism about the selfishness of people in Kira as well as a fear that she is Defiled Forever.
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Ménage à 3: The experienced Senna finds the geeky Gary amusingly easy to fluster when he interrupts her having sex with the equally experienced Matt, flirts with him ostentatiously, and extracts the promise of a date when she's next in town. However, her interest is strictly casual rather than romantic, and by the time she does return, Gary is a little more experienced, if still easy to confuse.
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Played with in The 100 Girlfriends Who Really, Really, Really, Really, Really Love You. No matter how many girlfriends he collects, Rentarou refuses to indulge in any kind of lewd acts at all. But that doesn't stop the more lustful girls (none of whom have actually engaged in intercourse with anyone) from trying to have their way with him and/or convince the other girls to do so.
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In The Sorcerer's Daughter, Siegfried is the resident Casanova, but, to his surprise, he falls in love with Odile, who is a complete innocent when it comes to romance. He pursues her in a very determined manner, and Odile is soon completely overwhelmed with feelings and falls head over heels for him.
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The Music Man: Discussed in "Sadder but Wiser Girl" and double subverted in the show. When Marcellus suggests setting con artist and ladies' man Harold Hill up with a Sunday school teacher, Harold rejects it, believing that innocent girls are more likely to ensnare you and get you to settle down than the experienced ones. As such, he subverts the trope by going after Marian Paroo, who is not only skeptical of Harold but is rumored to have slept with the old rich miser who left the library to her when he died. Marian is actually innocent of the rumors — the miser was a friend of her late father's — meaning she is technically still innocent in that regard, but Harold falls for her because when she finds out about his con, she chooses not to sell him out, ultimately downplaying the trope.
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Cruel Intentions: Kathryn invokes the trope as the premise of The Bet she makes with her equally morally and sexually bankrupt step-brother Sebastian: If he can somehow sleep with Annette, the exceedingly virtuous headmaster's daughter, she'll sleep with him. Sebastian is a verifiable Casanova, as part of his introduction in the film is him flirting with a girl in one scene and bedding her the next.
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Fifty Shades of Grey: Anastasia is a 21-year-old college student who is so innocent to the ways of sex that she has not even masturbated before. Christian, on the other hand, is a BDSM connoisseur who has had multiple partners from a young age. He is almost instantly attracted to her and begins to pursue her, despite her being a very ill match for him since she 1) has no experience with BDSM or subbing and 2) is horrified and turned off by most of it when she begins to understand exactly what Christian is into. The story exaggerates the dynamic so much that it acts as a Decon-Recon Switch of the trope, by showing all of the issues regarding boundaries and power imbalance that can come with such a relationship before arguing that those are all overcomeable obstacles since Love Redeems.
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Peach Girl: Despite what her appearance may suggest, Momo is a Naive Every Girl, who has never been on a date because everyone assumes she Really Gets Around and every guy that does approach her is only going for what they think will be an easy lay. While she herself pursues the equally dense and naive Toji, it's the Chivalrous Pervert and class flirt Kairi that pursues Momo as he's one of the few people who sees her for who she really is. Momo is not pleased ...at first; she ends up picking him over Toji by the manga's end.
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Confession Executive Committee has many couples, but the one representing this trope is that of Ken Shibasaki and Arisa Takamizawa. Ken is a teen playboy, a noted skirt chaser, and a very social guy. Arisa, while outspoken and upbeat, has no dating experience, very few friends, and is reluctant to make more because of a past incident. She doesn't like Ken's carefree attitude and tells him off for it, which makes Ken pursue her. Eventually this leads to him being more patient and affectionate while she opens up to his advances slowly.
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Sensual Phrase: Former High-Class Call Girl turned rock star, Sakuya, chases after the virginal and innocent Ordinary High-School Student, Aine. He initially plans on just selfishly using her and is a Fetishized Abuser for much of their early relationship, but he eventually falls in love with her for real.
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Crimson Peak: The youthful, innocent, and sheltered Edith Cushing is pursued by the dashing and worldly Sir Thomas Sharpe, who acts the perfect gentleman, seemingly averting the trope. In reality, Thomas is The Bluebeard, having married several women and allowed his sister Lucille to murder them so they can inherit their assets, and is also in a sexual relationship with Lucille. In fact, he and Lucille specifically chose Edith to be their next victim because of her naivete and inherited wealth.
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In The Year of the Rat:
The granddad is worried about Loveable Rogue Zhar possibly seducing The Ingenue Ryska since Zhar is a well-known ladies' man and will dump her, while Ryska has no dowry and her good name is her only hope to secure a marriage. The granddad needn't have worried: after a fleeting She's All Grown Up realization, Zhar views Ryska purely as his best friend, while she doesn't even think of him romantically.
Played straight when several years later Ryska (still virginal and very naive when it comes to romance and sex) starts having Belligerent Sexual Tension with Chivalrous Pervert Alk, who is very fond of embarrassing her with Double Entendres and bawdy gestures. Eventually, they do fall in love and end up in a Maybe Ever After, though Zhar is still worried Ryska is too young and naive for Alk.
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In The Snow Maiden, the eponymous girl is a Tragic Ice Character who is quite literally frigid, only able to feel platonic love, and extremely naive when it comes to matters of romance, let alone sex. It leads to tragic consequences:
Lel, who is The Casanova to the point that villagers with grown-up daughters or young wives don't want to let him in their houses, falls in love with the Snow Maiden. However, her childish responses to his flirting (for example, when he asks for a kiss, she thinks he means Platonic Kissing, and later she tells him that she wants to be his bride but finds the idea of being a wife ridiculous) eventually annoy and exasperate him, and he finds love with the less beautiful but more passionate Kupava. After seeing them together, the Snow Maiden pleads for her mother the Spring Beauty to give her the ability to love and is granted her wish, after which the sun melts her.
Mizgir, who previously, by his own admittance, slept around for fun and won many a girl's favor thanks to his wealth, likewise falls for the Snow Maiden. However, she doesn't even understand his passionate pleas and advances, and he frightens her (even before he outright crosses the line). Thanks to Break the Haughty courtesy of the Wood Spirit, Mizgir gets the idea of asking for consent, and due to gaining the ability to love, the Snow Maiden does accept him... for the grand total of a few minutes before she melts, and he is Driven to Suicide.
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Dreamgirls: When the Dreamettes become backup singers for Jimmy Early, who is a notorious womanizer despite being married, Jimmy instantly takes a liking to Lorrell, the shyest and mousiest of the three, and eventually woos her (The Movie makes it clear that he took her virginity as well). After the 7-year Time Skip that occurs between acts 1 and 2, it becomes clear Jimmy won't divorce his wife to marry Lorrell, despite leading her to believe otherwise for almost a decade. She eventually tires of his crap and finally ends the affair.
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Star Wars: The Old Republic: The female Smuggler and Bounty Hunter PCs and their respective class story Love Interests, Corso Riggs and Torian Cadera. Both PCs have multiple opportunities for Optional Sexual Encounters and in general are more worldly than their male partners: Corso had a very old-fashioned, tradition-bound upbringing, while Torian is 18 and so inexperienced with women that, when he gets her at gunpoint on Taris, she has the option to flirt with him to get him to point the gun away long enough for her to disarm him.
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Kimi ni Todoke ~Soulmate~: Eiji used to pickup girls and had several girlfriends even before falling in love and dating Sachi meanwhile Kurumi never had a boyfriend and had not even gone on a single date. He asked her out and Kurumi even denies that their first date is actually a date. Lampshaded by Kurumi as she thinks that she's at a total disadvantage when dealing with him.
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In Howl's Moving Castle, The Casanova Howl first meets Sophie when she is a sheltered young Shrinking Violet, and when he tries to flirt with her, she gets scared and runs away. Later, after Sophie gets turned into an old woman and gains a lot of sass and backbone, they switch to a more or less equal footing; though Howl's bright smiles still occasionally make Sophie weak in the knees.
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The Last Herald-Mage Trilogy has a Reincarnation Romance between thirtysomething Vanyel, who survived the death of his beloved as a teen, and the seventeen year old reincarnation of said beloved. Because Vanyel is Famed In-Story and it's Lonely at the Top he's been all but celibate in the meantime, but Stefan has had a very colorful last few years and on meeting Van immediately becomes a gay Ladykiller in Love, who worries that his experience repels the very pure Van. It does not. Stefan's able to leverage his greater experience to convince Van that it's not an Unequal Pairing where a powerful older man seduces a younger one. He knows what he wants, and he's pursuing it.
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Sinfest: In a rare example of an experienced female chasing an inexperienced male, Fuschia, a succubus, starts to pursue a relationship with the self-described nebbish bookworm Criminy because he treated her kindly and seemed more interested in her as a person than he was in the sexual services she offered as part of her employ with The Devil. It begins her Heel–Face Turn, in fact.
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In Brig Scarlet Flamingo:
Walter, who has had many lovers during his years as a sailor and later a pirate, seduces Amelia, whose experience of any sort of relationship is limited to drunken men pinching her in taverns. Amelia, who is also lonely, is smitten very quickly, but their relationship is cut short when Walter is killed.
Downplayed with Gerald and Isabel Ernscott. Theirs is a May–December Romance, and several side-stories featuring them make it seem that Gerald is the experienced partner in contrast to naive Isabel. However, other side-stories, published later, reveal that Gerald briefly dated one girl at school, it was very chaste and fizzled out quickly, and then he stayed a Chaste Hero until meeting Isabel, which makes him just barely more experienced than her.
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Fire & Blood: Daemon is a dramatic Byronic Hero who Really Gets Around. He's also a prince, who has very little accountability for his actions. He's said to "have an especial fondness for deflowering maidens."
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Bridgerton: Daphne Bridgerton is The Ingenue. Her innocent beauty, purity, youth, and grace are so laudable that the Queen of England bestows upon her the title of the season's Diamond: the most eligible young girl making her debut in society. Simon, the Duke Of Hastings, is a Reformed Rake whose reputation from his college days precedes him. Simon doesn't necessarily pursue Daphne so much as the two, after entering a Fake Relationship filled with Belligerent Sexual Tension out of convenience, fall in love over time. But the dynamics of this trope are still present. Daphne's older brother and current Lord Bridgerton, Anthony, tries to block their relationship because of Simon's reputation and known lack of desire to wed, Simon teaches Daphne about masturbating, and Daphne's ignorance on sex becomes a major plot point later on when she realizes it's not that Simon can't have kids, but he refuses to, pulling out every time they have sex.
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Discussed in Stardust. When young Victoria Forester and her friends talk about her suitors, one of the friends says that the only good thing about a match with 45-year-old widower Robert Monday would be his sexual experience. The entire conversation is Foreshadowing the fact that Victoria does end up with Robert (and by the time the wedding is near, Victoria is already pregnant).
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Spartacus: Blood and Sand:
Crixus, who has slept with many women previously and has been having a sexual relationship with Lucretia for several years (albeit he doesn't have much choice in that), falls in mutual love with Naevia, Lucretia's virginal body slave. They engage in a Secret Relationship as Naevia is forbidden from sleeping with anyone without her masters' permission. When the truth is revealed Naevia is forced into sexual slavery as punishment, destroying her innocence, although she and Crixus are able to overcome this once they're reunited and continue to have a happy relationship.
Gannicus is a Chivalrous Pervert who regularly indulges in casual sex, especially after his First Love ended disastrously. He eventually falls in love with Sibyl, who is shy and inexperienced with relationships. Interestingly, Gannicus actually declines to sleep with Sibyl at first because of her innocence, thinking he'll "ruin" her, but Sibyl ends up pursuing him, winning him over with her compassion and sincere love for him. 
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Earth's Children: Jondalar Really Gets Around — while this is considered normal in his culture, he's often noted for his attractiveness and Sex God skills. Despite having had many lovers over the years, Jondalar has yet to find a woman he wants as a life partner, much to his disappointment. In contrast, Ayla has lived alone for three years without even seeing another person and knows very little about sexual pleasure; she's technically not a virgin and has even given birth but that's because she was raped. Initially, Jondalar thinks Ayla's mixed responsiveness to his flirting is a sign she's uninterested, while she just doesn't understand how to convey her feelings. Once they've cleared up the confusion, Jondalar happily offers to show Ayla what consensual sex is like and she eagerly agrees; they realize they're in love shortly afterward. Jondalar likes the enigma of Ayla being a self-sufficient, mature woman who is also guileless when it comes to intimacy; she is happy to be with a considerate lover who cares about her happiness.
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Vermeil in Gold: While neither Vermeil nor Alto have been in love before, its made clear Vermeil is quite practiced in the arts of pleasure (whether she has had sex before or not admittedly being unknown) as she has zero hesitation french kissing Alto soon after meeting him, and exhibits plenty of other well-practiced techniques of seduction. Alto, who has zero experience, is understandably overwhelmed, while Vermeil finds his innocence endearing (not that she dislikes it when Alto starts demonstrating more confidence either).
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House of the Dragon: When the series begins, Princess Rhaenyra is a young 14 year old girl whose closest brush with romance is her Pseudo-Romantic Friendship she has with Alicent. Her uncle Daemon on the other hand is at least 15 years her senior, unhappily married, and a frequent visitor to brothels where he has a long-term lover. Daemon spends much of the early episodes grooming Rhaenyra into falling for him, seemingly both out of a genuine attraction between the two and because being with her would bring him one step closer to becoming King, something he very clearly covets. This climaxes in Daemon taking Rhaenyra for a night out on the town, seducing her, and almost having sex with her in public at a brothel. The ambiguity around whether or not he took her virginity (he implies to the king he did) can ruin her as a marriage prospect and King Viserys essentially exiles him to Dragonstone for doing it.
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A Condition Called Love: Hananoi, a notorious Serial Romeo, pursues Hotaru, an Oblivious to Love, Naïve Everygirl. Hotaru agrees to go out with him specifically because she wants to know if it's possible for even someone as agnostic to love as she is to love and be loved in return. Much of their relationship revolves around Hananoi trying his best to wait for Hotaru's feelings and comfortability to catch up to his and holding himself back so as to not spook her off.
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How a Realist Hero Rebuilt the Kingdom.
Played for Cringe Comedy in volume 5. Duchess Excel Walter, the 500-year-old admiral of Friedonia's navy with numerous descendants, takes it upon herself to give The Talk to the virgin Souma and his wives-to-be (who include one of her granddaughters). She attempts to make the former a practical lesson, which Souma frantically talks her out of. Though it's left somewhat ambiguous whether she actually meant it or if she was just messing with him for laughs.
From volume 10 on, Souma becomes the more experienced party, having become the father of twins with his Top Wife Liscia a few months before marrying his Battle Harem (they had Their First Time in volume 5). He deflowers his other four brides over the week following their group wedding and coronation, beginning with Aisha.
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In Outlander, Claire, after ending up in the 18th century, falls in love with and eventually gets married to Jamie. She was/will have been/is already married in her native 20th century and asks Jamie (previously single and several years her junior) on their wedding night if he is all right with her not being a virgin... only for him to awkwardly confess that he is one.
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Semelparous: Kaminoi Youko is in her 20s and certainly more sure of herself than the virginal Aratsugu Yorino. After they're partnered up, they quickly engage in a Teacher/Student Romance. The story doesn't directly state that Youko has had prior lovers, but the first time they have sex in volume 3, it's stated that Yorino has never even had an orgasm by herself before whereas Youko, who's the one who initiated and is leading their lovemaking, clearly knows what she's doing.
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180 Angel: Lilith is definitely not a virgin, and she ends up having a crush on Sam, who had never been in a relationship. She fell in love with Sam because she was genuinely trying to get to know her better and help her without any ulterior motives. Sam also didn't know who Lilith was when they first met. Unusually for this trope, Lilith isn't really a sweet-talker and frequently embarrasses herself in from of Sam, and Sam can be really smooth when she wants to.
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House of Anubis: Eddie was a flirty "bad boy" who quickly developed a crush on Patricia because of their constant bickering. While Patricia liked him back, she refused to admit it at first, which was initially just played as her being a tsundere... until she kissed him and then began to avoid him entirely, becoming quite anxious because it was her First Kiss ever and Eddie was the first guy she ever attempted to be romantic with. Her failure and stress in the romance department continued to make their relationship difficult even after they got together, with their temporary Offscreen Breakup happening because Patricia panicked again.
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Attraction Tropes
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Duo Tropes
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Flirting and Courtship
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Love Tropes
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Romance Novel Tropes
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Sex Tropes
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