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Anime and Manga
- Love Hina has Samurai girl Motoko forced to try becoming more feminine after Keitaro (more or less accidentally) defeats her in a duel. She's too violent to be good at it, though. She then feels that she has "failed" Keitaro, so she announces that she will commit seppuku, ritual suicide.
- Ironically, she intends to commit suicide by slitting her stomach open. This is the traditional masculine version of seppuku. A Proper Lady commits suicide by slitting her throat. If Motoko were to actually go through with her suicide, she would have failed at femininity again.
- Generally the case with Akane in Ranma ½. Played for laughs, of course, whenever Ranma shows up and turns out to be immensely better than her at any feminine task.
- In Kashimashi, tomboyish Tomari tries to teach the recently-female Hazumu how to act like a girl. Although she does impart some wisdom, mostly all she manages to do is prove that, even when she was in a male body, Hazumu was more girly than Tomari.
- In Berserk despite Guts' memorable reaction to seeing Casca in a dress, the femininity is somewhat dampened a moment later when she elbows him on the jaw for staring. She does this in front of several noble ladies who are very embarrassed to have seen it.
- In one late episode of the first season of Sailor Moon, Usagi joins a club designed to help create "princesses", thinking that she could be more lady-like after the revelation that she was Princess Serenity. She flops with flying colors, the only thing she was good at was Frisbee throwing. The other girls join in and the only other people who flop are Rei and Minako. Which is a good thing when it stands revealed that the club was a trap by Kunzite, and Ami and Makoto need saving along with the other girls there.
- In part of the Love Letter Lunacy in episode 4 of Kin-iro Mosaic, local Tomboy Youko attempted to be more feminine as Aya commented it's more likely a girl, rather than a boy, to send her a love letter. She tried to emulate the more girly Aya, which looked completely fake.
- The third episode of Steel Angel Kurumi Encore had Kurumi attempt to be more ladylike when she believes Nakahito isn't attracted to her anymore. Nakahito is more worried for her safety as she gets more and more desperate before she finally suffers a Heroic RROD and faceplants on the floor.
- In K-On!, when Ritsu is selected for the role of Juliet in a class play, her friends try to help her prepare for the role by forcing her to act more feminine in real life, banning her from talking like a boy and giving her a constant stream of etiquette instructions all through their light music club meeting. The attempted makeover lasts exactly one afternoon before Ritsu snaps and goes right back to being her normal self again.
Yui & Mugi: Sit like a lady!Ritsu: I can't do that while I'm playing the drums!
- My Monster Secret does a version of this trope based around sexiness rather than traditional femininity. Youko isn't a Tomboy, but rather The Ditz, so her concepts of sexiness are questionable at best. She strives to become a "Cool Beauty", but her idea of a sexy pose looks like it came from a Super Sentai show, and several characters completely missed the fact that she shows just as much cleavage as her perverted friend Shiho because she has absolutely no idea how to properly flaunt her larger-than-average bustline.
- To that point, there's an entire chapter in the manga where Youko engages in a "sexiness battle" with Akari-sensei and Principal Akane, with a tied-up Asahi's Nosebleed serving as their "gauge". All three of them fail so spectacularly that Rin (Asahi's Granddaughter from the Future and a rather literal Moral Guardian) approvingly declares it a "sex-free sexiness battle".
- Lucky Luke: One story has Calamity Jane taking etiquette and cooking lessons. Needless to say, she can't help but swear like a sailor and her cookies are inedible. When threatening a group of men with her rifle unless they eat up, one of them opens his shirt and says "Fire!"
- One issue of Archie had Veronica teaching Betty to be more ladylike (which was essentially her teaching Betty to be identical to her mannerisms.) Everything was going well until she spotted a couple of kids playing catch, which ends with her joining them and landing in a tree in retrieving the ball when it got stuck up there. While Veronica is annoyed with the turn of events, the kids all laud Betty as a hero.
- The plot of Miss Congeniality.
- Mulan has the title character screwing up the traditionally feminine "matchmaker" process.
- Sylvia Scarlett has the title character after only a short time of dressing up as a man somehow incapable of passing as a woman (she now has short hair, and masculine mannerisms so even wearing a dress is an Epic Fail).
- In The Untold Story, the female police officer dolls herself up to impress the guys at the office but ends up going too far and looks like a prostitute.
- The Princess Diaries has the awkward Mia who takes princess lessons and gets a makeover to which her friend tells her that she sold out. She's still clumsy after the lessons.
- Sarene in Elantris is a princess who tries to be traditionally feminine, but fails spectacularly at girly activities, leading to her having trouble fitting in with the court.
- Hilarious example in Monstrous Regiment by Terry Pratchett, where an entire platoon of women pretending to be men have to go undercover in "drag", and fail miserably at it. For extra hilarity, the one actual male in the group has no trouble whatsoever passing as female.
- In the Chronicles of the Kencyrath, heroine Jame is an Action Girl par excellence and all around harbinger of chaos being a nascent avatar of destruction will do that for you, and needless to say, when she's forced to try and become a proper Highborn lady in the third book (translation: elaborate dresses, lots of sewing, power wielded primarily through political intrigue, and very little in the way of physical activity), hilarity ensues. And by hilarity, we mean "rampant anarchy".
- Several decidedly unfunny examples happen with Brienne of Tarth in A Song of Ice and Fire. She is so huge and ugly that attempts to dress her in a feminine way make her look worse than she does in armour, and while it provides some amusement for other characters, it only increases her feelings of being a freak unloved by all. Arya Stark has some examples as well, like tearing new dresses and being terrible at needlework.
- Shows up in the case of Shallan Davar of The Stormlight Archive. She tries to be traditionally feminine to win over Adolin, but fails epically, breaking into the middle of one of his tales of derring-do to ask how he can poop in Shardplate. Luckily, Adolin finds her being herself even more attractive, and they are quite thoroughly in love by the end of the book.
Live Action TV
- In Degrassi Junior High tomboy LD tries to be more feminine, including getting a makeover from her best friend Lucy. It fails and the makeup makes her look like a clown.
- Sam from iCarly did this to get a guy's attention, with Carly giving her help to embrace her "inner daffodil". She ends up fighting with another girl by the end of the episode. As it turns out, the guy was impressed and said he didn't want to date "some daffodil."
- Happens on Naturally Sadie when Sadie gets upset after being called 'son' and tries to become a girly girl. Her mother is away so she gets advice from Hal (of all people). By the end of the episode, she has managed to find a balance between tomboy and girly girl.
- In Miranda, large-boned Miranda attempts to glam herself up with hilarious results. First she's oblivious to the fact that the only shop stocking glamorous clothing in her size is actually crossdressers' shop. Then she's flattered to get hit on by a genuinely nice guy who clearly (to everyone except Miranda) thinks she's in drag. Her bubble is finally burst by her best friend's astonished:
Miranda! Why are you dressed as a transvestite?!?
- Ami from Pretty Guardian Sailor Moon tried make up when having a slumber party with Usagi and Naru, however, due her status as the Cute Bookworm of the show, she didn't have much experience, so she naturally over did. Note that her failure wasn't fueled by being a Tomboy as she is a normally feminine girl, but it was rather a result of her dorkiness and preference toward intellectual activities (And the fact she didn't have any friends until she met Usagi).
- In the Frontier Circus episode "Stopover in Paradise", Ben romances the tomboyish owner of a local ranch. She attempts to become more feminine for him, but has trouble, especially with her high heeled shoes. Ben eventually tells her to take them off so he can teach her to dance properly.
- In Persona 4, Chie has this problem. She's obsessed with martial arts films, isn't scared to pick a fight when someone is in trouble and eats almost nothing but steak. She likes being who she is but doesn't like that the other sex treats her more like one of the guys instead of a girl. Her attempts to be more feminine usually don't end well, such as her cooking. You can say that her fear of bugs is cute, however. This is actually the right choice to move the social link in a positive direction.
- Makoto Kikuchi from The Idolmaster was raised like a boy and has a lot of female fans who admire her looks, but what she really wants is to be more feminine and get more attention from boys. Unfortunately, her attempts to be more girly rarely ever succeed.
- In Mass Effect 3's Citadel DLC, Female Shepard and Miranda Lawson, the former a marine for her entire adult life and the latter a reformed former member of a terrorist organization, both realize just how weird their lives are and attempt to act more normal by talking about traditionally feminine things. They can't even complete a single sentence.
- During Kjelle's supports with Severa in Fire Emblem Awakening, Severa forcefully attempts to give Kjelle a ladylike makeover. While she fails miserably with the makeup, she does succeed in developing better manners. Of course, Kjelle finds it entirely pointless and scorns the entire process.
- From Gunnerkrigg Court: Kat, the more tomboyish of the protagonists, puts on makeup for the first time in order to impress Alistair, a New Transfer Student at her school. She fails horribly, and Annie's there to assure her that she's lovely just the way she is.
- Falco from Namir Deiter tries to act more feminine for a while, when she's worried Cedric will go back to Tipper.
- Sal Walters in It's Walky! attempts a femininity makeover with the intention to get her old boyfriend back, and fails miserably. When she tries again later on, she deliberately skips the lipstick.
- The Nostalgia Chick tried to invoke kawaiiko for a while, but could never pull it off. Now she's settled for being a ladette Psychopathic Womanchild. Her friend Nella was given a visit by the makeover fairy. She resisted and the fairy ended up putting a bag over Nella's face because there was nothing she could do for her.
- Kung Fu Panda: Legends of Awesomeness: Tigress, in "The Princess and The Po" tries to pose as the princess to protect the actual princess from the bad guy. She tries to do the Princess Ceremonial Dancing Song. She can't sing, and she can't do graceful ladylike (although the real princess is not much better).
- Arthur: Francine tries to be feminine for one day, picture day, where she goes to school in a dress and doesn't play kickball during recess so she'll be presentable for her photo. But she ends up playing anyway, and being scruffy in the picture.
- An episode of The Legend of Tarzan has Terk wanting to be feminine to attract another gorilla. She realizes by the end that it's completely unnecessary.
- The Hey Arnold! episode "Helga's Makeover". She does this to attend Rhonda's sleepover but reverts to her old self after refusing an avocado cream mask.
- In The Legend of Korra, Korra decides to try out that "powdering your nose" thing she's heard about. The ensuing cloud of dust leaves her coughing.
- In the first series, Toph and Katara's minisode in "Tales of Ba-Sing Se", Katara takes Toph to a spa, and Toph is so stand-offish about getting dolled up they need to get a hulking spa worker to hold her down, and then they touch her feet...
- Azula makes an attempt at being a typical teenage girl during the Beach Episode, complete with coaching from resident Girly Girl Ty Lee, only for her efforts to literally crash and burn at the end.
- Subverted in Recess with both girls. Spinelli is entered against her will into a Beauty Pageant and is initially awkward with the femininity - but ends up as one of the finalists. Similarly bookworm Gretchen gets convinced into going to the beauty salon with Ashley A and enjoys it.
- Also subverted in The Weekenders. Lor is given a makeover by two Valley Girls when they hear a popular guy likes her. She shows up wearing a skirt and a girlier hairstyle. Though the reactions of her friends (and the guy in question) is a straighter example. Lor backs out when she hears she's supposed to get made over even more - including plastic surgery.
- An episode of CatDog had tough tomboy, Shriek, trying to make herself "a real woman" to get Dog's attention. After she is finally successful at looking and sounding more feminine, it backfires when everybody, except Dog, begins hitting on her.
- Played with on an episode of As Told by Ginger. The girls use makeup for picture day, and end up looking like clowns. Justified, however, because a) they are young and have not been taught how to use makeup properly and b) they made their own makeup out of things like gravy and cranberry sauce.