A character is subject to a Gender Bender, Disguised in Drag, or Sweet Polly Oliver scenario, and now has to appear in public as the "opposite" sex. Their problem is they haven't had the benefit of the years of acculturation that naturally-born members of the other sex have had, and/or suffers Genre Blindness to the differences in social rules for members of the other sex. Hilarity Ensues.
Grammatical gender can complicate things in many languages such as when a character is talking about himself/herself. Adjectives and/or nouns might have different endings depending on the grammatical gender of the antecedent. For instance, consider a sentence like "I'm an excellent driver." The words corresponding to "excellent" and "driver" might change if the speaker is male or female. A few languages (Japanese most prominently) have gender-specific first-person pronouns. English is an unusually gender-neutral language, and thus very forgiving to victims of sudden sex changes and those in need of last-minute opposite-gender disguises.
This is a frequent source of comedy material in works that feature sudden or recent transformations. By contrast, "experienced" Wholesome Crossdresser and Gender Bender characters aren't subject to this sort of comedy of manners — they've had enough time beforehand to learn and prepare, and comedy centering around them generally focuses on exposure, and other characters' reactions.
One common variation involves characters mostly falling for a Wig, Dress, Accent disguise. Even though it's blindingly obvious to the audience that the character is fumbling about in a wildly gender-inappropriate manner, other characters react as if it's just slightly odd.
The Trope Namer, though not an example, is a Joe Jackson song. There's also a film called Different for Girls, but, ironically, it doesn't feature any examples of this trope, as its main character underwent their gender transition for years by the time of the movie.
Disguised in Drag, Sweet Polly Oliver, and Fish out of Water plots are frequently centered around this trope. Naturally, the Third Law of Gender Bending mandates these characters be placed in these situations as often as possible. If the character complains about it, someone is bound to respond with Welcome to My World.
Compare Man, I Feel Like a Woman . Contrast with The Mind Is a Plaything of the Body.
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Ranma One Half plays with this trope. On one hand, Ranma has no "feminine modesty" because he was raised to be a manly man. On the other hand, he's just savvy enough to take advantage when indulging in ice cream, candy, and other sweets that might carry an "unmanly" stigma. Plus he's savvy and shameless enough to charm waiters into giving him free food just 'cause he's a cute girl. In one episode this trope was gender flipped; he suffers a concussion and starts to think that he's primarily female. Hilarity Ensues because he temporarily forgets how to act like a man.
The second episode of Kashimashi: Girl Meets Girl deals with this — and then for the rest of the series, the absence of these sorts of incidents is used to point out how naturally feminine Hazumu is.
Played with, and ultimately averted for the Once a SeasonDragged into Drag episodes of the Slayers anime; most of the situations that Gourry is thrown in in the first season did not require the gender-specific Japanese Pronoun gap, and most of the dialogue that occurs during it and the second season is gender-neutral. In the second season, Zelgadis manages to get around the aforementioned gap with polite speech and a less-formal introduction. Given that the series is a comedy, feminine gestures weren't required, and in the third season, Gourry is in a mermaid getup for less than two minutes, so nothing applies there.
Maomarimo offers a different take on this trope in that it's mainly focused on how the protagonist's gender bender makes things different for other people, primarily her twin sister and her best friend.
Early in Earth X, it's revealed that Thor has been transformed into a woman due to Loki's meddling. Thor remains in this form until the end of Universe X. During the comics' run, this involuntary switch causes Thor continual difficulties; she keeps saying things like "I'd sooner kiss Hela's lips." (Loki finds this remark very amusing.) Before long, other characters are lampshading it with sexist remarks like—"You're a woman now, Thor. We don't say things like that." It's not clear whether this is a Shout Out to the mythological example below, but it seems likely.
Early issues of Mantra dealt with this as Lukasz adjusted to being in Eden's body (and to suddenly being a single mother).
While discussing Some Like It Hot, a movie reviewer asked Tony Curtis why his "Josephine" was so much more feminine than Jack Lemmon's "Daphne". A laughing Curtis explained that he was so scared to be playing a woman (or a man pretending to be one) that his tightly wound body language could be read as demure and shy, traditionally feminine traits, whereas Lemmon, who was completely unbothered, and "ran out of his dressing room screaming like the Queen of the May," kept much more of his masculine body language.
Subverted by Mrs. Doubtfire, whose acting career (especially his specialty in voice acting) enabled 'her' to pass quite well and the illusion is only occasionally spoiled by the main character's hatred of the new love interest in his ex's life. It also helped that he wasn't trying to portray a young/sexy woman (as that probably would have raised more questions), instead acting as a world-travelled, wise grandma-type character.
Mark Twain's The Adventures of Huckleberry Finn: In chapter 11, Huck disguises himself as a girl when he goes ashore hunting for information about what has transpired in town while he's been on the river. His disguise, which includes a face-concealing bonnet, could have been successful, had Huck known how to behave like a girl, but Mrs. Loftus, the woman he tries to deceive, sees through him quickly and tests him. For example she tosses him a ball of yarn to see whether he knows how to catch things in the skirt of the dress he's wearing.
Averted in The Marvelous Land of Oz, the second of L. Frank Baum's Oz books. Tip, the boy protagonist, spends the entire book searching for the lost Princess of Oz only to discover near the end that he'sthe lost princess. While he expresses some initial reservation at the thought of becoming a girl it's mostly because he wonders what his friends will think of him. After he becomes Princess Ozma nothing more is ever said about her backstory even though the princess is a veryGirly Girl. Given that it was a children's book published in 1903, it's not surprising that there wasn't much examination of this trope.
The body swap segment of Night Watch has one with Olga trying to give Anton a quick primer on how to behave while he is borrowing her body, finishing with a comment that it is a good thing the timing worked out in such a way that she didn't have to teach him about dealing with the menstrual cycle. Anton's reply is hilarious in deliberately showing men's perceived ignorance on the subject. He says that, like every other TV-watching man, he knows that you hold a tampon in your fist and pour dark blue liquid on it. Even with this crash course Anton doesn't quite manage since his body language is still distinctly masculine.
Polly recounts learning to walk like a boy: girls only swung their hips; boys swung everything in what she concludes is an attempt to look bigger and fiercer. Since she spent several years seving in a pub she has experience and is able to give tips to another Sweet Polly Oliver.
Ironically they later need to disguise themselves as women in order to infiltrate the enemy stronghold. Their CO decided he has to be the one, and he is the only actual male amongst the entire squad. More ironically, this is because the girls have "male" mannerisms, like constant scratching, burping and farting and swearing. The CO decides that they'd have no hope to ever pass for women, and takes the job for himself. When they later try to infiltrate as women the guards attempt to seize them believing them to be men in disguise. A quick bit of exposure convinced them otherwise. Their CO on the other hand made it in without any problems.
The children's novel Bill's New Frock has Bill wake up and find himself a girl. Bill finds no difference. None at all.
In "The Song of the Lioness" quartet, the main character Alanna experiences this...but not when she disguises herself as a boy, since she started that when she was quite young. No, the problem occurs when she later "pretends" to be a noble lady. Her friend immediately recognizes her, even at a distance, since no 'lady' would walk like that.
Bosom Buddies relied heavily on this trope in early episodes. By the second season, most of the main characters were in on the "secret," and the focus was often more on generic "buddy comedy" situations than on crossdressing per se.
"Emily" Howard, the crossdresser character in Little Britain, is a variant of this. Most of the time the problem is that his ideas on how ladies are supposed to behave dates from the Victorian times, but occasionally he'll slip into very male mannerisms and speech patterns (e.g. when repairing a car engine.)
In the Farscape episode "Out of Their Minds," Rygel runs into this problem. He's stuck in another male's body (Crichton's), but he is not used to a humanoid body. When he has to relieve himself, he does not know how to hold it and then has to get instructions on how to go in the corner.
The Star Trek franchise had a few of these over the years:
In the Star Trek: Voyager episode "Body and Soul" the EMH inhabited Seven's body for most of the episode, resulting in him flirting with a female crewmember and being flirted with by a male.
A similar occurrence happened in "Renaissance Man" where the EMH briefly took on B'Elanna's appearance and was forced to behave affectionately towards Tom in order to maintain the ruse.
TOS episode "Turnabout Intruder" in which Dr. Janice Lester, an old lover of Kirk's, forces him to swap bodies with her.
Deep Space Nine's "Profit and Lace", where Quark becomes a woman for an episode to drive home the gender unfairness of Ferengi society.
Quantum Leap had Sam jumping into women's bodies in multiple episodes. As with all leaps, Sam still perceived his body as his own and not the body of the person he leaped into. (It always took the reveal of looking into a mirror or reflective surface to tell what he looked like this time.) Only others saw him as his leaped-into persona. He therefore didn't have to deal with any of the biological aspects of womanhood (usually) but still had to deal with the social aspects. In one such episode, "What Price Gloria?", he uses the inverse to his advantage to strike back at his leapee's sexist, womanizing boss: the leapee is a stunning blonde woman, but Sam manages to convince her boss that "she" is really a man by describing in gleeful detail a number of uniquely male experiences that a woman could not possibly have had, such as what it feels like to be kicked in the groin. The Unsettling Gender-Reveal that ensues is pure Schadenfreude.
On Family Matters, when Laura went to buy her first car, she observed that boys got deals she wouldn't normally. She disguised herself as a boy to see if that would get her the same treatment a real boy would get. She got a quick course from Steve Urkel in how to behave as a boy, and returned to the dealer. It started out working, but her disguise broke down at some point... only for her to discover that girls have their own means of manipulating the price should they choose to use it.
Its appearance in Classical Mythology makes this trope Older Than Feudalism. The Greek hero Achilles was forced by his mother, the goddess Thetis, to hide at the court of King Lycomedes disguised as a girl; Thetis wanted to prevent her teenaged son from dying at Troy. Since it was prophesied that Troy would only fall if Achilles joined the invasion, the other Greeks were desperate to find him. Having tracked him to King Lycomedes' court, and figuring that Achilles was in drag, Odysseus went to the court disguised as a traveling merchant. In one version of the story, he found Achilles because he was the only "daughter" interested in the weapons and armor he was selling as opposed to jewels and dresses. In another, Odysseus cries that invaders are approaching the city and Achilles grabs a spear and runs towards the gates instead of running for safety like the other daughters.
A Norse Myth involves Thor's hammer being stolen by a giant and ransomed for Freya's hand in marriage. The Aesir decide to feign cooperation... by sending Thor and Loki to the wedding disguised as women. Thor, disguised specifically as Freya, is told to keep his veil on and his mouth shut, which he does (Loki, an experienced shapeshifter and Trickster, doesn't need similar instruction). Thor doesn't, however, get the point that a woman wouldn't scarf down most of the wedding feast and drink most of the beer in the least delicate way possible. Only Loki's frantic fast-talking ("She hasn't eaten much recently; too excited, you know") kept anyone, especially the groom, from catching on until Thor retrieved the hammer. He then proceeded to Kill 'em All. Thor was not fond of giants.
The point of the webcomic Misfile. Not only has the main character gone on a semi-permanent Gender Bender, the world has been retroactively changed so that he has ALWAYS been a girl. Ash soon finds out that it's a lot easier to get service in stores, get away with starting fights in school, and so on. The difference in his/her relationship with his/her parents is a chapter all its own. Unlike most examples Ash finds the Positive Discrimination aspects just as disturbing as the negative ones because they serve as a constant reminders that he's now on the distaff side of the Double Standard. Taking advantage would only serve to further erode what remains of his beleaguered manhood.
In one arc, Tedd (disguised as his girlfriend) is persuaded to do this to experience how things are different, with some suggestion he does this anyway to test that sort of thing out. Elliot is forced into a little of it, and his duplicate Ellen misses a few cues as to 'normal' feminine behaviour. Then again, she also yells out 'Booyah! I'm still one of the guys!' when left out of a girl-to-girl chat. Ellen has issues.
Shive tends to put sexual identity and sexuality down to physical things; transformation guns on default "add" heterosexual attraction for the sex they've made you to your original orientation (so a heterosexual becomes bisexual, and a homosexual becomes heterosexual), because the original purpose of the transformation gun was for assisting breeding for populations low on either sex. The one aversion of this tendency, Ellen-who-was-Eliot, unfortunately wound up looking like an incidence of No Bisexuals, since she'd been the only one and then retreated from that position.
Given how often Exiern milks laughs out of these experiences of its barbarian hero-turned-heroine, it's not surprising that a subplot about a cure attempt that backfired would end up focusing on the different for girls experiences (skirts, corsets) of the resulting Gender Bent priests...including one who is enjoying herself entirely too much.
It's in most of the origin stories for the TG characters of the Whateley Universe. The extent snd duration varies from author to author and from character to character.
The title character in The Saga of Tuck averts this in the beginning, as Tuck is so scared of discovery when his girlfriend dresses him up that he acts like a demure, shy young girl. Later, as other women in the story sharpen his imitation, this trope is lampshaded. Some girls who admit they find dresses and makeup intimidating also lampshade this.
There are literally thousands of original TG stories posted on the web (The Fiction Mania site alone has more than 15,000 stories on it) and most of them are based entirely on this trope — and little else, unfortunately.
episode "Bend Her," Bender undergoes a sex-change operation to compete as a woman in the Robot Olympics.
Bender/Coilette: I need more lipstick! Much more! Ooh, yeah! That's the stuff! Men love it when you really glob it on. Leela: No, they don't. Amy: No way! Bender/Coilette: Oh, please! Every man wants a tramp. No wonder you girls aren't married. I tell you, men are so much better at being women.
Another episode featured Leela posing as a man to enlist in the military (and keep her friends alive like she always does). However, the only error she made was slapping her CO for a congratulatory butt-pat. Most of the situation's humor came from Zap Brannigan's "feelings that are weird and deeply confusing".
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.
In the last part of Neutopia, everyone swaps gender. The guys just use this as an opportunity to get free drinks.
An early episode of The Fairly OddParents, "The Boy Who Would Be Queen". Timmy pokes fun at the female gender and in punishment Wanda turns him into a girl. He quickly takes advantage of his new form "Timantha" to spy on his crush Trixie Tang so he can get her the perfect birthday present.
Timmy: Why would I wish I was a girl? *laughs* *changed*
In the short animation Geraldine, a man wakes up to find that he's spontaneously become a girl. The short is about him adjusting to the change. Then, just as he's gotten into the swing of life as a woman (at the altar, no less), he changes back, with as little explanation as the change that started the short.
A lesbian feminist journalist, Norah Vincent, decided to replicate Black Like Me with gender instead of race and found that men perceived her as having effeminate mannerisms while she was disguised. (The book is called Self-Made Man: My Year Disguised as a Man..) She gained a lot of sympathy for the ways in which men force themselves to conform to gender roles as confining in their own ways as women's. She began by being nervous about whether she was acting properly manly, but later realized that it helped her fit in, because all of the (actual) men were doing it too.
"I passed in a man's world not because my mask was so real, but because the world of men was a masked ball."
This happened to a fair share of Transsexuals. While they identify as their gender, that doesn't mean they necessarily "act like" a boy or girl (or know the social differences). This could be because their personality is just boyish or femininine, they weren't raised as their gender, or various other reasons.
Transitioning transsexuals (from male to female) may notice their sex drive changing from a male sex drive to a female sex drive. Short version: male orgasms are more "flash in the pan" than female orgasms; quicker to build, quicker to go away.