No matter how flawless the Sweet Polly Oliver's disguise at fooling her male peers, there is some primordial part of a man's brain that sees through the disguise... and is attracted to their new drinking buddy.
This is especially true for The Casanova, whose refined "babe-dar" can detect estrogen even when the eyes can't. Of course, this will get very confusing and distressing to the unwitting male admirer. They'll be turned on and not know why, and if they're not too bright might say "have I met you before?" (which they have, only as a woman).
Expect the poor lech to have a lot of sexual confusion about his "feelings" for "another guy", and be incredibly relieved when she stops masquerading. Polly Oliver, if not oblivious to her effects, will (depending on the jerkiness of her admirer) feel guilty or gleeful. If she would normally pursue this guy romantically, she may reveal the ruse to mixed relief and feelings of betrayal.
It's rare for the man to actually be gay or bi in this situation. However, it's more common (especially in William Shakespeare) for a woman to fall for "Oliver" and only give up when the disguise is revealed or, these days, to not care.
Compare Attractive Bent-Gender, and Unsettling Gender-Reveal (for when finding out the love interest's actual gender makes them the wrong orientation). A subtrope of Gender Reveal.
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Anime and Manga
There's an example with Nagisa in Urusei Yatsura. He looks just like a girl, but Ataru and Mendo actually get suspicious by the fact that they, despite going after everything in a skirt, aren't attracted to "her". Ataru instantly realises Ryuunosuke's real gender as well, and goes after "him" along with all the girls.
In Rose of Versailles the female main character is disguised as a boy to be a bodyguard of the princess. Her fellow bodyguard develops a crush on her and gets rather confused.
In Hana-Kimi, Nakatsu feels conflicted because he thinks he is falling in love with Mizuki, but he also believes that Mizuki is a boy. Unfortunately for him, when Mizuki is finally revealed as a girl, Nakatsu finds himself in the loser side of the Love Triangle.
Some would argue that he was always on the loser side of the triangle. Nanba, the ladies man Dorm RA, on the other hand proclaims that he knew he was right about Mizuki being a girl all along, because his ladies radar never lies.
In the historical manga Kaze Hikaru, the main character Sei (disguised as a male samurai) has a large number of men chase after her with varying degrees of seriousness. In an interesting twist, most of them don't sense she's a girl; they are unrepentantly chasing after 'him' in the hope of a homosexual relationship, following the historical samurai tradition of homosexuality. Early on in the manga, one of the men enamored with her almost discovers her gender— by way of Attempted Rape.
Subverted in Girls Saurus, where the entire student body of the boys' school Tsubasa goes to is attracted to him because they think he's really a girl masquerading as a boy. Later, a lesbian completely falls for him... even though she actually knows he's really a guy.
It takes a bit of prodding from a Trickster Mentor before Penguin Revolution's Yuzuru Narazaki recognizes his attraction to Yukari Fujimaru for what it is. Once he does, he decides that If It's You, It's Okay and confesses his feelings to "Yutaka," still completely oblivious to the fact that Fujimaru isn't actually male.
Ranma ½ references this trope in one storyline that occurs shortly after Wholesome Crossdresser Ukyo joins the series as Ranma's final Arranged Marriage. As part of her "masquerade" as a boy, Ukyo attended an all-boy's junior high school. There, she came to the attention of another Wholesome Crossdresser, a boy named Tsubasa Kurenai... who promptly declared he was in love with Ukyo and harassed her in pursuit of a relationship. Until the storyline in question, she had no idea that Tsubasa had actually seen through her disguise and believed him to be the homosexual version of this trope, attracted to "his" Bishōnen looks. Akane and Ranma, meanwhile, believed a straighter version of this trope- aka that Tsubasa was a girl who had fallen for Ukyo under the mistaken belief that the Bifauxnen was actually a guy.
Kill Me Kiss Me is a manhwa originally created by Korean author Lee Young-you revolving around two identical cousins of different gender who end up switching places, so the girl can get near her crush. The boy agrees due to the fact that they each attend all-girl/all-boy schools. The girl is a much better fighter than the boy, attracting the attention of her crush, who has the exact confusion mentioned above. Meanwhile the boy is tormented by all the girls that have a crush on 'her' that cannot be dated because of the true gender.
Another manhwa, Love In The Mask, has a tough girl who's forced into being a male bodyguard, apparently because a girl wouldn't be taken seriously. She has a crush on a boy who views her as his little brother who he's always tussling with... and napping with... and cares about more than anyone else... and at one point uses her toothbrush after they shared her bed and dreams he's kissing a girl who looks like his "brother" (just how close are brothers in Korea??). Later they play Romeo and Juliet in an all-guy school play, to the fury of another guy who knows her secret and has a crush on her. Oh, and another guy also develops a crush on her when she's dressed as Juliet. The girl she's guarding also has a crush on the first guy and often wonders why she's jealous of two male friends.
Upon Sou's and Mashiro's first meeting in After School Nightmare Sou thinks of Mashiro as a cute girl— despite Mashiro's act as a normal man. Sou is, however, not troubled by his attraction to Mashiro.
Of course, Mashiro is not neccesarilly a man nor a woman.
Inverted in the anime adaption of Karin, where a flashback shows Ren thinking this was the case with his roommate, based on how he felt attracted to him. It turns out the guy was really a guy, and Ren was just reacting to his stress. At least that's what we're told.
Subverted in Angel Diary, in which Bi-Wal seems to see through Dong-Young's disguise but in fact they met long before the story began.
While he's not sweet on her, Gintoki's, um, trusty radar knew that Kyuubei was really a woman in Gintama.
Inverted in Mai-Otome when it's hinted that Shizuru feels something for "Prince Takumi"; but since it's also hinted that she's not really into guys she (correctly) suspects he's actually his female bodyguard posing as him.
In one of the latest chapters of Nononono one of Nonomiya classmates has a rather vivid dream with her visiting him in his room, after waking up he is greatly disturbed by a realization that he just had a wet dream about someone he considers "a perfect male specimen".
Kodaka in Boku wa Tomodachi ga Sukunai has to keep reminding himself that Yukimura is a boy every time he thinks that he's cute. Coupled with Kodaka's increasingly obvious Selective Obliviousness, this results in him expressing more attraction to Yukimura than the girls in the club who are all generally more important. Upon the reveal, his first reaction is actually irritating at Rika for some gibberish she told Yukimura that kept making her believe she was a boy when she wasn't.
Chiharu Eniwa of Girl Got Game find himself feeling something for Kyo Aizawa, a girl who is cross-dressing as a boy in order to join the school's famous boy's basketball team. While he doesn't outright question his sexuality, he does freak out over how cute he finds "him."
In ½ Prince Gui falls in love with Prince, Feng Lan's male avatar in a game word that doesn't usually allow Cross Players. In a slight subversion, he just rolls with the idea that he might be gay and declares that he'll love Prince no matter what sort of person 'he' is in real life.
In the hentai Midnight Panther, the Big Bad King Bad murdered his parents the king and queen in the backstory because he found out he was adopted, meaning his younger brother Lukish would get the throne instead of him. When Lukish saw him, he freaked out and fell off the castle's roof and into a river. King Bad was distraught because he had always been fond of his little brother. Very fond, to the point that years later he can't get it up because he keeps thinking of Lukish. He starts laughing maniacally when he wonders if this means he's not straight. As it turns out, Lukish was actually a girl raised as a boy all along. She also survived the fall and was rescued by the old lady who is in charge of the titular group of assassins.
Ouran High School Host Club's Haruhi is mistaken for a boy by the Host Club in episode one and is recruited as their newest member. Even before she's revealed to be female, their leader Tamaki shows signs of having begun to fall for her, enough so to make one of the few unpleasant girls at the host club get jealous of her. The rest of the girls that visit the club all continue fangirling over Haruhi.
Marvel 1602 had a rather interesting subversion with a Love Triangle involving the Expys of Scott Summers, Jean Grey, and Angel. Jean was posing as a boy to avoid rousing suspicion about Javier's school (no such thing as officially educating girls in the real 1602 England, much less co-ed schools), and was romantically involved with Scott. When she tried befriending newcomer Inquisition-escapee Angel, Scott becomes jealous, figuring that Angel like everyone else knows she's really a young woman. (He gets gigantic-size hints, but fails to parse them.) Eventually, Scott discovers he didn't, and apologizes for being such a jerk about his mistaken territoriality...and Angel responds, "You were not wrong. I saw a boy...but I believe I was in love with that boy."
Happens in an issue of Weird War Tales with an officer in a POW camp during the American Civil War being extremely relieved to learn that the "drummer boy" he was attracted to was actually a girl. And then the zombies show up...
In the Zelda fanfic The Weekly Hyrule News, this happens between Link and Sheik. Played with in that Link realizes he wasn't sweet on Sheik/Zelda because he picked up on her real gender subconsciously, but because he's bisexual. Incidentally, it's well-written.
Some Mulan fanfics have used this trope with Shang and "Ping" since the film avoided it.
The Bet, a SasuSaku fanfic by Blade Redwind is the epitome of this trope, questioning-his-sexuality and all. (Wish someone knew more fics like these!)
Film — Animated
In Mulan, we have Captain Shang, who grows close with young soldier Fa Ping, an awkward klutz who eventually Took a Level in Badass and earned everyone's respect and friendship. When he finds out that "Ping" is in fact a girl (namely Mulan), he is of course shocked, particularly because during those times, a girl joining the army is a crime punishable by death. Fortunately, Mulan had saved his life earlier and he repaid the debt to her by merely abandoning her. When she manages to save the day a second time, Captain Shang's feelings for her become obvious to everyone except perhaps him.
In The Nostalgia Chick's review of Mulan, The Nostalgia Chick jokes that Shang was probably relieved that "Ping" turned out to be a woman, since it means he's still straight.
Film — Live-Action
Victor/Victoria plays it differently than the usual Gayngst of this trope. Marchand (the guy) is initially repulsed by the idea of having a relationship with another man, but eventually decides that it doesn't matter. He tells Victor he doesn't care if Victor is a man and kisses him. Victor then reveals herself to be a woman. Marchand says he still doesn't care and kisses her again. While it's true that he's happier to be with a woman, there's no sense of extreme relief when he finds out because he loves Victor/Victoria as a person either way.
The live-action movie version of Rose of Versailles shows Fersen being extremely relieved at discovering that Lady Oscar is, indeed, a lady - and admitting that "I was beginning to wonder about myself".
"I didn't want to touch you. I didn't know why. I thought there was something wrong with me. I loved you...
A rare Bi the Way version happens in Sorority Boys, where three frat boys dress in drag to infiltrate a rival sorority. The sorority's president falls in love with one of them as a woman and is extremely upset when the ruse is up. However, she's more bothered by the trickery than the fact that he's a man, and they get back together in the end.
This is a major plot device in Tomboy. Laure introduces herself as a boy, and spends most of the film falling in love with a local girl as a boy. It isn't until the last 10 or so minutes of the film that the object of her affection learns of her sex.
Plot point in Brand Upon The Brain. The young hero falls in love with Wendy. Wendy however is after the hero's sister. She disappears and returns as Chance, a teenage boy. The hero instantly develops a 'boy crush' on this stranger.
Happens in the Hong Kong film He's the Woman, She's the Man, with Leslie Cheung playing a record producer looking for new male talent and ending up falling for a girl who got an audition disguised as a boy.
The Mexican film Los Rivales is based around this. There is also a minor character who is a man disguised as a woman; since "she" is an heiress, a local landowner sends his two dimwitted sons to court "her".
Played with in Pamela Kaufman's historical novels, in which Richard Coeur de Lion falls for the disguised heroine because he thinks she's a boy. Strangely, actually having sex with her does not disabuse him of this notion. (Considering Richard I was...ahem...rather fond of his minstrel Blondel, amongst others...) Squick!
It only gets better. Late in the novel, the squad has to infiltrate a castle dressed as serving girls. The only one who can convincingly pass for a woman is the male captain. And many of the castle guards find him to be a very pretty lady.
From Jingo, "One of the minor laws of the narrative universe is that any homely featured man who has, for some reason, to disguise himself as a woman will apparently become attractive to some otherwise perfectly sane men with, as the ancient scrolls say, hilarious results. In this case the laws were fighting against the fact of Corporal Nobby Nobbs, and gave up."
Poor Jamie Fletcher, the teenage ship's boy in L.A. Meyer's Bloody Jack series, beats himself up mentally for quite a while thinking that he is inappropriately attracted to fellow shipmate Jack (actually Sweet Polly Oliver Jacky). Luckily, she likes him too and eventually reveals herself to him.
Théophile Gautier's 1835 novel Mademoiselle de Maupin is probably the first work to spell out this situation and use it as a major part of the story. The book itself is loosely based on the life of 17th century swordswoman and opera singer Julie d'Aubigny, who didn't disguise her sex, but did dress in men's clothing to put on fighting exhibitions and engage in duels, and enjoyed affairs with both male and female lovers.
Subverted in Marion Zimmer Bradley's Hawkmistress!, where Orain has feelings for Romilly when she is dressed as a boy. However, it turns out Orain is actually gay, and he loses interest once Romilly's true gender is revealed.
Subverted in Delia Sherman's Through a Brazen Mirror. The king had been denying to himself that he was gay; initially he was delighted to find out that his crush was a woman — now it was okay to admit he was attracted! So he required her to dress in woman's clothes (which she was uncomfortable doing); but that only made him realize, wait, that really wasn't what interested him, and finally face the truth.
In The Thurb Revolution by Alexei Panshin, hero Anthony Villiers' old friend Fred Fritz confesses to Tony that he's become oddly attracted to young David Clodfelter. Villiers, more perceptive, or at least more consciously perceptive, realizes that David is not only a girl, but Gillian U, the girl Fred's father (the Emperor) has been trying to fix him up with. A snatch of conversation in the next book indicates the engagement has been made formal.
In Mary Stewart's The Last Enchantment, Merlin is puzzled by his attraction to his new boy apprentice, Ninian, who turns out to be a girl, Niniane.
In Ann Pratchett's Bel Canto, a group of young paramilitaries take a bunch of hostages, and over the weeks relationships form between the two groups. Interpreter Gen is attracted to one of the paramilitaries, a pretty young boy. The boy turns out to be a girl. Gen is relieved.
Inverted in one of the Judge Dee stories by Robert van Gulik: a young woman came to the judge, asking for advice because she'd lately found herself strangely attracted to another girl living close to her. As it happened, Judge Dee already knew that "the other girl" was actually a young man who'd gone undercover to investigate the suspicious death of his sister — and the young man had admitted to the judge that he was quite attracted to the girl who was now (needlessly) worrying that she might be a lesbian.
There was a Colombian mini series called "Cartas de Amor", about the rocky relationship between Cupido, a very convincing Bifauxnen who works as a match maker thanks to her talent to write the titular Love Letters and was called to solve all the romantic conflicts in a little neighborhood, and Manuel, a unrepentant The Casanova who likes the state of romantic indefinition in his neighborhood (because he can get the unsatisfied women for him) and sees Cupido's actions as opposed to his own interests. When all their conflicts are solved and her real gender is revealed, many neighbors are not very convinced of either her femininity or his manhood, so they want proofs. Then, Cupido says something in the line of "the main proof of his manliness is that he could see the woman in me behind all the costume and the farce."
One Star Trek: Deep Space Nine episode finds Quark strangely attracted to his waiter (who turns out to be a female disguised as a male).
In one episode of Northern Exposure, Chris the DJ takes a sabbatical at a monastery and finds himself overwhelmed with lust for one of the other monks, in spite of "him" always wearing "his" hood up in a largely shapeless robe and having taken a vow of silence. Near the end the monk breaks her vow of silence to help sooth Chris's inner confusion. (In spite of being pretty relaxed in every other way he has apparently always been all about women prior to this.)
Inverted in an episode of Reno 911!. Lieutenant Jim Dangle, who is gay, finds himself having an inexplainable attraction to the female homeland Security agent Suzy Kim. At the end of the episode we discover Suzy Kim is a male in drag, and is not a Homeland Security agent, but a con artist.
This revelation also prompts a discussion by the force (brought up by Garcia) whether or not jacking off thinking about a guy who looked like a girl makes you gay. Jones insists that it does, of course, even if most of the men on the force liked Kim.
This relationship really happened, it's in his memoirs. Casanova insists he isn't sinning (in that particular way, that is) because he can tell she's a girl, but she (still claiming to be male) points out that he doesn't know that and is in love with her already. In real life there was quite an interval between perceiving that bulge in her pants and learning that it was fake, during which time the poor bastard was terribly confused. He records a lengthy lecture she gave him on what would happen if she let him check and he found out he was wrong, namely that he wouldn't be able to stop loving her and would come up with all kinds of arguments about male homosexuality being purer and more intellectual than heterosexuality, citing historical examples, until he wore her down — and he pretty much admits it. He also continues calling her Bellino (her masculine alias) interchangeably with Teresa (her real name) in the narrative for some time after revealing her actual gender; make of that what you will.
In Will and Grace, Jack (who's gay) finds himself attracted to a woman at a party. He starts doubting his sexuality until it's revealed that the "woman" was actually a man all along.
The first episode of Brazilian miniseries Copas de Mel had Mel disguising as a man to travel with the Brazilian team for the 1958 FIFA World Cup. She develops a crush for the wardrobe boy Jiló, and after Brazil wins:
Used in the Swedish mini-series The Girl At The Stone Benchnote swedish= Flickan vid stenbänken when fraternal twins Arid and Rosilda both fall for the new servant "boy" Carl. Problem? Carl is actually Carolinnote The ad demanded a boy and a girl since the two were supposed to add female and masculine influence to both of them. Theater maniac Carolin fixed that by strapping on a tuxedo., who seems to really enjoy to flirt with the girls who think she is a boy. Played to some really dark irony:
Head-Maid:(Noting that Berta, Carolin's sister, sees that Arid ignores her in order to chat with "Carl") Arid is not that interested in girls. I mean, he is not like Berta's brother. (Cut to "Carl" giggling over something Rosilda wrote in her "conversation-book" and kissing her hand)
Played even better when Arid finally comes out to Berta. Because she thinks his love for her "brother" is because Arid somehow notices the female Carolin inside (he doesn't), it gives him the most open minded acceptance any gay teen could hope for in 1914, focusing on that "Carl" was a charlatan, not worthy of him. Contrast when his sister told her about her perfectly normal True Love and was instantly pushed back, with her using words like "That's impossible!" and "That is Wrong!". Poor girl.
Happens in The Nanny, Fran dresses up as a guy to get into a men's only club to talk to Mr. Sheffield. After a while she reveals who she was resulting in his classic:
Mr. Sheffield: Oh thank God. I thought all those years of working in musical theater had finally caught up with me.
In All Shook Up, Orsino is portrayed as a Lady Killer In Love... with a 'man'. He explicitly has to deal with suddenly having 'homosexual' feelings, and even fully accepts and chooses to act on them before the masquerade is revealed to him.
Ditto some productions of As You Like It. Though Orlando must at least have started to suspect Rosalind's identity.
Also, some productions of Cymbeline may emphasize this between the main character Imogen and Cadwell/Guiderius (and Polydore/Aviragus.)
It's one of those situations where the princes have several lines expressing the noble lines of Imogen and how they truly love her. She's their sister. So arguably, they could be stating that they feel oddly close to her/him like a brother.
A Very Potter Musical subverts this in the sequel when Dumbledore is only attracted to Umbridge because he thinks she's a man in drag.
Final Fantasy V: Bartz and Galuf fawn over the sleeping Faris the pirate captain before they discover she's really a woman.
Persona 4: Kanji Tatsumi feels this way towards Naoto Shirogane upon meeting "him" for the first time, which of course only serves to make Kanji's already-present issues of gender confusion worse. Kanji's sexuality remains ambiguous at best for the rest of the game, but it's clear he still has strong feelings for Naoto, especially after Naoto's true gender is revealed.
Princess Waltz: Even before Arata realizes Chris Northfield is pulling a Sweet Polly Oliver, he finds himself extremely attracted to "him", causing everyone around them to wonder if they are commiting Ho Yay. It only gets worse when Chris admits to really being a girl, which takes what was already strong attraction and kicks it into overdrive. Considering the game is an H-Game, and Chris is remarkably underendowed for a girl (Saber from Fate/stay night looks less manly than Chris, and she's arguably Saber's Expy), but Arata finds her incredibly hot anyway, which for this genre is an amusing but rather touching subversion.
For the uninitiated, H-Game women usually have some variant of Ms. Fanservice or large breasts as a rule, making the subversion more jarring.
Joshua in Rule of Rose was in fact Wendy all along, forcing Jennifer to relive her childhood struggles and make her remember their mutual past.
More in the book than the game, but in the former Edward Kenway admits a definite attraction to Mary Read's male guise of James Kidd.
An odd example in Video Game Confessions—Zelda often goes around in her Sheik outfit, feeling that she has more freedom as both a man and a commoner. She's explaining all this to Dominic when Link shows up and starts hitting on her. Link explains that yeah, he's still dating Zelda, but he likes to "swing his sword both ways." Link assures "Sheik" that Zelda is cool with it. Oddly, "he" doesn't seem to believe that.
Zapp Brannigan in the Futurama episode "War is the H-Word". He finds private "Lee Lemon" intriguing in very uncomfortable ways, to the point that he's visibly relieved when Leela drops the disguise and punches him in the face.
Zapp: Leela! So it's you I've been attracted to! Oh God, I've never been so happy to be beaten up by a woman! Leela: Let's do it again sometime.
In Clone High, Joan dresses up as "John Dark" to play basketball. She adds a mustache. Kennedy begins to feel attracted to her. As Kennedy's adoptive parents are a gay couple, he has a lot of soul-searching done.
Cleopatra (the show's Alpha Bitch) was also attracted to "John Dark" (although she was MUCH more aggressive about it than JFK). At the end when Joan reveals herself, Kennedy shows relief at not being gay, while Cleopatra is just intrigued.
In Family Guy Chris Griffin becomes infatuated with a tomboy he completely believes to be male, and after she kisses him he writes in his diary that he kissed "him," but didn't want a serious relationship. When she revealed herself to be a girl to the dimwitted Chris, they became a couple after some disbelief, exacerbated by the fact that Chris is incredibly awkward around girls but wasn't this time until the reveal.
In Code Monkeys Mary feels that she isn't being respected enough by her boss so she decides to dress up like a man and call herself Mitch. She tells everyone at work that Mary died, and that she wanted Mitch to continue his work. Her co-worker Jerry showed signs of having a crush on Mitch the moment he showed up, fantasized about him, and even admitted he was gay for Mitch in front of a crowd before he kissed him and blew her disguise when her mustache came off.
Jerry: I'm not gay?
Dave: No dude, you're totally still gay!
Never outright stated in Cybersix, but Lucas really, really likes Adrian; Cybersix's "male" alter ego.
Flipped around with Lori, a female student who's madly in love with Adrian and has no idea that "he" is really a beautiful woman. This gets very awkward in one episode, when she follows Adrian home and catches a glimpse of "him" (now dressed as Cybersix), talking to someone out of sight. Cybersix was actually talking to Data 7, but Lori figured it was Adrian. Hilarity Ensues as she tells Lucas how some woman named Cybersix is dating Adrian on the sly, much to his displeasure.
Inverted with Anne Bonny and Mary Read, a legendary pair of 18th century female pirates. When they met, Anne Bonny was openly female, but Mary Read was a Sweet Polly Oliver. Mary eventually revealed her gender when Anne developed a crush on her. They later went on to become Back-to-Back Badasses. Though it's not known how far their relationship went after that, by the time their ship was captured and the crew brought to justice, both women were pregnantnote Anne presumably by her lover, Calico Jack, and Mary by hers, the ship's doctor. The real Crowning Moment Of Awesome being that, since they were both pregnant, neither could be sentenced to death, despite a long and unashamed career of piracy until after the children were born. Unfortunately, Read died after childbirth in prison. Bonny disappeared from the record, but is believed to have been rescued by her merchant father and lived a long and presumably straight life in colonial South Carolina.