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Anime and Manga
- Kashimashi: Girl Meets Girl. Surprisingly, it's a girl that suddenly pays attention to the guy-turned-girl, as does the guy-now-girl's best male friend.
- Subverted in The Day of Revolution as the very idea of a romantic relationship with any of her former True Companions has the gender-bent protagonist thoroughly squicked. Doesn't seem to discourage the boys, though. Then again, they weren't all that shy even when she was a guy.
- Your and My Secret: After Uehara and Momoi switch bodies, Momoi almost immediately starts dating her best friend Shiina, who doesn't know about the switch, and Sengbongi, who figures it out but doesn't mind, makes several romantic/sexual overtures towards Uehara. It's an interesting case, since while the body switching did facilitate both relationships, it's implied that there was existing attraction pre-body switch.
- Inverted in Kämpfer: Kaede doesn't seem to be interested in male Natsuru. Suddenly Natsuru turns into a girl, and at first sight Kaede falls in love with "her." It gets creepy when we find out Kaede's a Psycho Lesbian who Does Not Like Men, and that she turned Natsuru into a girl for this very reason; this of course arguably makes the trope played straight.
- Not surprisingly there's a hentai manga about this. A male student finds himself body hopping into females at certain points in time, and he uses every occasion to sleep with a local Jerk Jock Cassanova. Though as soon as he's left the girl's body (paying no attention to the girl who just had been taken over as she's usually in a daze of orgasmic pleasure) it turns into Ho Yay as he pleads his love for the jock.
- Subverted in Sekainohate De Aimashou when a Human Alien prince slips an Ordinary High-School Student a Gender Bender potion only to get Incompatible Orientation instead. And then Double Subverted when the two hook up, get married, and have children by the end of the story.
- Sekirei has it's own way with this trope. Homura has an unstable gender, but mentally identifies himself as male. At the start of the story he was physically male, and had been trying to find an Ashikabi who was female. However, as time went on his body began reacting to main character Minato, who is a heterosexual male. As a result, Homura began turning into a woman. It's not clear if the transformation was complete by the time he was finally "winged", but the character now has breasts as well as more feminine features, and is pretty annoyed and uncomfortable with the whole situation. Poor, guy/girl.
- Played with but ultimately subverted in Nozomu Nozomi: his budding romantic interest in best friend Yasu may have started Nozomu down the road to womanhood after his mysterious Gender Bender, but it's her outrage at Yasu's horndog lewdness that convinces Nozomu she's truly become a girl.
- Kanata of Kumo Desu Ga, Nani Ka? was originally a male before being reincarnated as a girl. She still identified as a man in her mind which resulted in her suppressing a growing affection for her male friend Shun. After a near-death experience where Shun saved her she started identifying as female and shortly after started giving Shun hints about her feelings.
- Runaways, with Xavin and Karolina. Karolina is gay and engaged to Xavin, who appears in a youthful male image that he believed would please her. Being a Skrull, for whom changing shape and sex is as difficult and important as changing the color of ones hair, Xavin is not bothered by this, and happily assumes a female form to make Karolina more comfortable. Some drama that might or might not have happened later revolved around confusion over Xavin's "true" sex, and Karolina's assertion that Xavin is really a woman, despite the fact that even Xavin points out that he/she (Even the characters become confused over the proper pronouns) is not only one or the other.
- The issue becomes significantly more stable, however, when Xavin unconsciously reverts to a 'default' female form during an argument.
- The Avengers: In Earth-3490, the Civil War created by the Superhuman Registration Act is averted. Why? Because Captain America and Iron Woman get married. Interestingly, they both get married in costume, which causes a double take upon turning the page because Iron Woman's gender is surprisingly ambiguous if you ignore the veil. And instead of the stock 'standing together at the altar' image, they're making out in front of the church.
- Of course, soon after that came out, it was put on The Internet...and Tony's beard got photoshopped onto 'Toni''s face, with varying levels of looking actually beard-like.
- Ovid's Metamorphoses has the rather touching story of Iphis and Ianthe, which involves crossdressing, arranged marriages of the enjoyable variety, and a magical last minute genderswitch that saves the day, making this trope Older Than Feudalism.
- Played with in Orlando: A Biography by Victoria Woolf. The title character is courted by a man posing as a woman. Said man has Single-Target Sexuality, and simply quits posing after Orlando's Gender Bender. Unfortunately for him, Orlando finds him irritating either way (and later falls in love with a Bishōnen.)
- In Albanian folktale "The Girl who Became a Boy", the eponymous crossdressing girl impresses a king and is married to his daughter. The princess cannot be satisfied by her new husband, and seeks impossible tasks to get rid of "him". In the last of these, the husband is cursed with a Gender Bender... and is finally able to satisfy the needy princess. They live happily ever after.
Live Action TV
- Victor/Victoria and the BBC Casanova series. In both cases, a guy is prepared to have a relationship with a man, but then luckily finds out they are a woman.
- Oddly enough, Quark gets caught up in two distinct instances of this trope on Star Trek: Deep Space Nine:
- Quark's brilliant new assistant has fallen in love with him, greatly distressing Quark who is not interested in males but values the subordinate's insights and abilities. Unfortunately, the reveal that this Ferengi is actually a female posing as a male in order to have a chance to earn profit does not come as any real relief to Quark because females are forbidden from earning profit (or even wearing clothes) and if anyone ever found he got business advice from one, he would be ruined.
- Another episode that never happened has it go exactly the opposite way as Quark's mother tries to champion the cause of equal rights for females. Quark ends up masquerading as his mother's female protege (too well) resulting in the man she was supposed to be negotiating with trying to seduce him. When another character intrudes in order to expose his ruse, Quark exposes just how far he went to champion his mother's cause.
- Similarly done in the Blackadder II episode "Bells" (where young girl Kate dresses as a boy and becomes Blackadder's servant "Bob").
- The Doctor Who comedy skit "The Curse of Fatal Death" has the Doctor regenerating four times in ten minutes — his companion (and fiancée) copes with seeing her beloved turn into Richard E. Grant, Jim Broadbent and Hugh Grant, but when the final regeneration is female she sorrowfully announces that the Doctor is, quite literally, not the man she fell in love with. The Master, rather keen on the Doctor's new Joanna Lumley-shaped body, is only too happy to step in.
- Interestingly averted years later in Doctor Who proper, when the good ship Doctor/Master did finally get two big damn snogs with one of them (the Master) now being female, but it had nothing to do with Jumping the Gender Barrier. Writer Steven Moffat, who also wrote "The Curse of Fatal Death", went on record saying that gender isn't actually a factor for Time Lords when it comes to attraction and that there is no gender barrier for these characters.
- The Buffy the Vampire Slayer episode "Him" features a high school jock with a jacket that hypnotizes women into falling for him. Hilarity, and drama, ensues as all of the female cast members begin doing over-the-top things to attempt to win his affection. In Willow's case, she's gay and one of the other female characters tries to get her out of the way by reminding her that said jock is a guy. But since Willow is also an incredibly powerful witch, she notes that this is a very minor problem and begins casting a spell to turn Him into a Her.
- In the Murder Most Horrid episode "A Severe Case of Death", Dawn French's character dresses as a man in order to impersonate a doctor. During the course of the episode she meets a man with whom she shares a slightly more-than-friendly chemistry. After it is revealled that Dawn's character is really a woman they pursue a romantic relationship.
- Dårfinkar och Dönickar. Isak finds out his new buddy Simon is actually Simone, and decides he like-likes her (they're twelve).
- In one series of FoxTrot strips, Jason has a nightmare (triggered by Kafka's The Metamorphosis) where he turns into a miniature version of his sister Paige. He frets that his guy friends will harass him when he shows up to school as a girl. Older brother Peter remarks "There are worse things than being made fun of"; enter Jason's Black Best Friend Marcus, holding a bouquet and love hearts floating around his head.
- Exalted has magically bonded pairs of people whose magic soul shards constantly reincarnate. Each pair is a Solar Exalt (Sun powers) paired with a Lunar Exalt (Moon powers, duh). However, the pairs don't always reincarnate in a gender that the other prefers (though bisexuality is common in Exalted, it is not universal). Some just end up forming platonic bonds that last the millennia of their lifespans. Or, the Lunar Exalt can pick up the Twin-Faced Hero knack... and change gender at will.
- This isn't exclusive to Solar/Lunar couples, either. Two of the most prominent Lunar elders are a couple. One of them has a habit of changing sex every decade or so, and the other is completely straight, and will only acknowledge their relationship when the other is currently a woman.
- Persona 4 has the interesting case of Kanji Tatsumi and Naoto Shirogane. The former falls in love with the latter at first sight, causing him to become extremely sexually confused. When he eventually comes to terms (via the Protagonist's help) with his new sexuality, his love interest is suddenly revealed to have been a woman all along, once again throwing him into confusion. A case of Jumping the Gender Barrier twice, with the same person.
- El Goonish Shive plays with this possibility when (normally gay, temporarily female) Justin and (normally straight, temporarily male) Susan kiss (and stuff, though it ultimately goes nowhere). Shive presents as the only outcome that could possibly have ended well, and given that the alternative would have been two good friends having a quick roll in the hay for all the wrong reasons, with no chance of a Relationship Upgrade due to Incompatible Orientation, that was probably a safe bet.
- Also has a straight example with Nanase and Ellen. Nanase was a closeted lesbian, and didn't even realize it herself until she met Ellen, her ex-boyfriend's Opposite-Sex Clone. It's complicated. And spoilery.
- Elliot and Justin tend to subvert this, as Justin is only attracted to Elliot when Elliot is male, but Elliot is only attracted to Justin when one of them is female, and Justin isn't interested in becoming a full-time girl.
- Any Universe where Tedd and Elliot are opposite genders seems to result in this happening. For example, Beta Tedd and Beta Elliot (Ellen) are in a relationship. In a non-canon story where Tedd is female due to some reality-warping mishap (which retcons that s/he always was female), s/he and Elliot are in a relationship.
- Sparkling Generation Valkyrie Yuuki has the main character guy-turned-girl Yuuki's female childhood friend wait until after he turns into a girl to show romantic interest in him. Though given the general degree of Genre Savvy in a comic which explicitly runs on Magical Girl Manga and Anime tropes a Romantic Two-Girl Friendship may just be mandatory.
- Misfile inverts this by having guy-turned-girl told by straight-friend Emily that she would love him in a heartbeat if he was a boy. Since Ash is fighting Gender-Bending's most seen law and thinks of himself as a guy, he assumes that Emily is interested, with bad results. They get over it.
- Also played straight with a male friend of Ash's; they met up after being separated for a while, and he suddenly tries to make out with her. Turns out her retroactive girl-self had a Relationship Upgrade with him...but Ash doesn't remember it, and isn't attracted to guys anymore. Cue awkwardness.
- The Dragon Doctors partially subverts this, as Mori and Sarin become a couple only after both of them change gender. Each admits to finding the other more sexually attractive in their current forms, though after Mori changes back to her original gender they continue the relationship even getting engaged
- Inverted in the Jet Dream Remix Comic, where before her transformation to T-Girl Harmony Thunder, T-Bird Squadron leader Jack Thunder had a Dating Catwoman relationship with Raven Red, leader of the Dynamic Dare-Dolls. Raven Red didn't react well to Harmony's change, due to Incompatible Orientation. (Harmony, however, seemed willing to give it a go.) The conflict pushed Raven Red over the edge into Psycho Ex-Girlfriend territory. She's now obsessed with either changing Harmony back into Jack (which all other characters know to be impossible), or killing her as a last resort.
- Sort of invoked in Something*Positive, where the gay Jhim hits on a woman he thought was a man from behind. He winds up having a good time on their date, though, discovering she's a lot like his female friend Pee-Jee, and later laments to her how he wishes he could meet a man like that. Since Pee-Jee had had a crush on him for years, you can imagine she was annoyed.
- Mentioned by Jake in Homestuck, as apparently he used to remark to Dirk that they were such good friends that he would totally go out with him if he were a girl. Dirk, for his part, is gay and in love with Jake. At least Jake admits in retrospect that he might have been leading him on a little. And the relationship might actually happen even without the trope being enforced, as later Jake begins to wonder whether it really even matters that Dirk is a guy.
- The relationship does, in fact, happen. It doesn't last, although that's due to personality issues with everyone involved, not anyone's orientation.
- Shortpacked! has a rather odd example of this. Originally Ultra-Car was, as the name suggests, a sapient car, whom all the characters treated as male. Meanwhile, Malaya is a human woman who had dated men and experimented with women, only to conclude she was straight. Then Ultra-Car switched to a Fem Bot body, Malaya comes to the conclusion that she's actually Robo Sexual, and the two form a relationship (although Ultra Car is asexual).
- Played with and ultimately defied in Exiern: Denver thought Tiffany's Gender Bent nature and general loathing of his female body meant his (Denver's) feeling would remain one-sided. Then he learns Tiffany's origin story and learns Typhan-Knee was gay and thinks things have worked out for the best. Tiffany chews him out for assuming that now that that's in the open, he'd be "free" to be in a relationship with Denver, ignoring Tiffany's still prominent issues with his involuntary gender bending. Ultimately averted (at least for now) when Denver chooses to stay behind and learn to control his newly-discovered draconic nature.
- In the Paradise setting, a number of stories feature involuntarily-gender-changed characters falling in love with someone of the gender they used to be, though they did not necessarily know them before the change. (In "After Hours", a woman who used to be a man fell in love with a man who used to be a woman.)
- This happens quite a lot on Literotica. Typically, a man gets turned into a woman and falls in love with his former best friend.
- Played with in Geraldine. A man turns into a woman inexplicably, has his (her?) best female friend help out, and years later turns back into a man, just in time to run off with said friend.
- After The Nostalgia Critic did a crossover with Diamanda Hagan, the fandom obviously shipped them. Problem is that Critic's a guy (if a feminine one) and Dia is a Psycho Lesbian. Solution? Make Critic a girl so they can have all the BDSM sex ever.
- Happened on Family Guy with a female Wholesome Crossdresser called Sam who Chris met. She kissed him when he still thought she was male. He said he just wanted to be friends (but privately noted it felt kinda good when "he" kissed him) before finding out she was actually female, after which he sort of thought a romantic relationship would be okay, except he had too much trouble talking to girls, a problem which he solved by pretending he didn't know she was female, thus subverting the trope - apparently he didn't really object to making out with a guy as long as other people wouldn't see it that way.
- Played with in Cow and Chicken. When the question of Chicken's gender is put on the table in one episode, after he laid an egg (it was actually a prank by The Red Guy), his best friends develop a crush on him (believing that 'he' is now a 'she').
- Inverted in American Dad! when Stan temporarily becomes a woman. Stan and Francine experiment with lesbianism, which doesn't work out. After Stan is turned back into a man, their sex life resumes.