Some tomboys are fine with their stereotypically masculine personalities or even thrive in it. Others hate the fact they're tomboys but have difficulties trying to change their behavior. They may try to invoke a Girliness Upgrade but this often results in Femininity Failure. No Guy Wants an Amazon is often a reason for them disliking being a tomboy. Whether they're fine with their tomboyish streak is another matter.
This appears often in Japanese material and is a point of Values Dissonance to many non-Japanese audiences. Due to Japanese gender roles, many female characters are embarrassed by seeming masculine and actively try to change it. It's comparatively much harder to find a non-Tomboy with a Girly Streak in Japanese media who is fine with their behavior than it is to find in American or British media.
If a character had tomboy angst in the past this could be why they Used to Be a Tomboy.
- Boku to Boku is about a tomboyish girl named Yuuki who befriends a Wholesome Crossdresser named Junichirou after she saves him from a chikan. Yuuki hates how boyish she is but everything she does results in Femininity Failure. Another crossdresser falls for her specifically because she's cool and boyish, but Yuuki herself wishes she were girly.
- Boyfriend is a oneshot about a girl who uses another girl as a Replacement Goldfish for the lack of boys at her all-girls school. Risa only likes Yuuko because she looks like a boy and she views her as one. She gets Yuuko to grow her hair out and start wearing skirts so she can see her as a girl. It's implied Yuuko didn't like being tomboyish much anyway.
- Himegoto - Juukyuusai no Seifuku: Yuki is a androgynous looking woman who wishes she was more feminine and hates her reputation as One of the Boys.
- Hime-chan no Ribon: The titular character Himeko is a funny, energetic girl with Boyish Short Hair who is seen by everyone as the biggest tomboy in the school. She has an insecurity that she is not feminine enough and actually wants to be like her sister Aiko, a soft-spoken, domesticated girl who is considered very beautiful. Himeko sees Aiko as a role model and the ideal woman.
- Ice Revolution: Masaki was Raised by Dudes and taught judo by her father. She hates how masculine she is and wishes to be girly however her attempts fail. All her peers still see her as very tomboyish or even as a boy. She gets into figure skating to become more feminine and gets a makeover over the course of the series. Though, Masaki still does best skating athletically rather than more "femininely".
- Love Live!: Rin is a tomboy who doesn't think she is attractive due to it.
- Mahou Sensei Negima!: Madoka has a lot features which makes her a tomboy (notably short hair and a husky voice), but an important part of her character is that she hates them.
- Monthly Girls' Nozaki-kun: Subverted with Kashima. When she got a cold which made her voice hoarse, she started mentioning how her voice is the only feminine thing about her and now that she lost it...she's happy because now she can pass off as a real guy.
- Otonari Complex has Akira, who not only is a tomboy but looks like a handsome boy. For the most part she's used to it, but she has deep insecurities over not being as cute and feminine as the other girls in her life or her childhood friend Makoto (her exact opposite in every way).
- Ranma ½: Akane Tendo is a Tomboy with a Girly Streak who's treated by everyone as a full-blooded tomboy. Problem is, Akane desperately wants to be girlier but like Yuuki above, all her attempts to be more feminine finish in failure and lots of her tsundere behavior to her boyfriend Ranma come from her frustration at HIM for being better at girly things when needed. It's strongly implied that her beloved mother's early death and being partially raised by her very girly older sister Kasumi has lots to do with it too.
- Sailor Moon: Makoto is a tomboy but one of the reasons she cooks and sews is to make herself seem more feminine.
- Tomo-chan Is a Girl!: The eponymous Tomo doesn't hate being a tomboy, not a bit...but because of her boyish qualities she's worried that her crush/childhood friend doesn't actually see her as a romantic option. The majority of the manga has her do various schemes to appear more feminine as a result.
- Urusei Yatsura: Ryuunosuke was Raised as the Opposite Gender and is a very tough and aggressive Bifauxnen due to her upbringing, but she really just wants to be feminine. She wants to wear dresses, put on makeup and date just like normal girls do. It's difficult since her overbearing father keeps foiling her every effort to be like a woman. As a result people keep treating her like a boy (or even mistaking her for a boy) and this is a huge Berserk Button for her.
- Between the Lines: Chapter 42:
In reality though, the gender of the #1 Level 5 esper was hardly male despite what their appearance might indicate.The constant confusion that people made about her gender pissed her off however she felt as though she would drop dead from embarrassment if someone saw her, regardless of whether they were a stranger or not in a dress or something girly. She wore those types of clothes from time to time however only on days where she did not expect to go out into the City.
- In The Cutting Edge: Chasing the Dream. Alex Delgado (Francia Raisa) is a tough, spicy amateur ice hockey goalie who, based on her body language, really doesn't like playing with the boys. After a few rough patches, and a coaching change on his end, she becomes Zach's replacement partner.
- Arya of A Song of Ice and Fire dislikes girly things because she's insecure about not being good at them, and wishes they weren't forced on her. The TV series changes it so that she just hates girliness.
- Iria Gai from Alice, Girl from the Future was quite upset at having no cooking skills once she fell in love. She learned quickly enough though.
- In The Stainless Steel Rat, Jim visits a planet where the traditional gender roles are inverted. One policeman complains loudly that his mother raised a tomgirl out of him while he wanted to be a househusband like dad.
- iCarly: Usually averted with Sam who clearly likes being a tomboy, but played straight in iMake Sam Girlier where Sam feels that a boy would never like her because of her masculine ways. She also tries a Girliness Upgrade but gets over it by the end of the episode.
- Buffy the Vampire Slayer: In Season 1 Willow gets annoyed with Xander seeing her as "like one of the guys" even though she's more nerdy than tomboyish.
- Lizzie McGuire: In one episode Lizzie worries that being good at football will stop the other boys from thinking she's not feminine enough to date. The Brawn Hilda of a coach teaches her An Aesop about this - while also revealing she sews her own dresses and goes line dancing on the weekends.
- 3rd Rock from the Sun: One episode introduces Janice, a tough, super-strong cop. Sally, another tough ladette, challenges her to an arm-wrestling match but Janice easily beats her. When Sally confronts her again, Janice starts crying and tells Sally that she is "soft inside", and hates being seen just as a "tough warrior" and not as a woman. Probably Truth in Television, since she was played by Chyna.
- "One Of The Boys" by Katy Perry is about a teenager trying to make herself more feminine so she won't seem so tomboyish anymore. Her crush sees her as a platonic friend or "little sister" instead of a romantic option.
I wanna be a flower,not a dirty weedI wanna smell like roses,not a baseball teamAnd I swear one day maybe one day you're gonna wanna make-out with me(Don't wanna be...)'Cause I don't wanna be "one of the boys""One of your guys"Just give me a chance to prove to you tonightThat I just wanna be one of the girlsPretty in pearlsAnd not "one of the boys"
- Makoto from The iDOLM@STER is a bifauxnen who has a lot of female fans who like her looks. She wishes she were more girly and popular with boys.
- Senran Kagura: Miyabi is well known for being a handsome girl who has a lot of female fans. She's bothered by it and she tries to have a more feminine appeal.
- Persona 4: Chie Satonaka felt jealous of her friend Yukiko Amagi because of her femininity and getting many of the boy's attention. Her Shadow manifested because of her obsession over dominating Yukiko because of Yukiko's reliance on her.
- A theme with Aoi Asahina's Freetime Events in Danganronpa: Trigger Happy Havoc is her slowly revealing how unfeminine her thought-process/lifestyle is and in the last event we hear her worry that she'll never find a boyfriend because of it. After "practicing" a Love Confession on The Hero (which only turns into a Femininity Failure), he tells her she's quite charming the way she is.
- Mion from Higurashi: When They Cry is One of the Guys and even refers to herself as an "old man". Despite this she secretly has a more feminine side and gets very upset when Keiichi gives Rena a cute doll because he deemed Mion "too boyish" for it. Mion's situation is more complicated than most examples. Mion has an identical twin named Shion. The two used to pretend to be each other often until one day Mion received a yakuza tattoo. The problem is Mion was really Shion, thus the girl everyone knows as Mion was born as Shion. Mion has to pretend to be a tomboy instead of a Girly Girl, and the other way for Shion, though occasionally their 'true' personalities come through.
- The Legend of Tarzan: In "Tarzan and the Enemy Within", Terk, the abrasive tomboy female ape, was having a crisis over how she viewed her tomboyishness as a hindrance to gaining the affections of a new male ape rescued by Tarzan named Gobu.
- All Grown Up!: Lil plays soccer and mostly wears pants. Although there have been a few episodes of the series where she does try to be more girly to fit in with the other girls, those episodes also emphasize, especially in the end, that she is a tomboy at heart.
- Star vs. the Forces of Evil: One episode reveals that Janna secretly likes the color pink, but she hates to give into gender stereotypes.
- Winx Club: In a season 2 episode, Musa complains that Riven, her object of affection, doesn't like her for this reason ("I don't think Riven could ever be interested in a tomboy like me").
- Thora Birch claims that her career declined into adulthood because she "wouldn't wear the frilly bows". Having become a star in the 90s alongside many other tomboy actresses, she had a hard time fitting in with the Turn of the Millennium that favoured blonde Girly Girls.
- Numerous women wrestlers who get signed to WWE are tomboys who are unprepared for the all the feminine things required to look good on TV. The Bella Twins say that while Natalya taught them how to wrestle, they had to teach her how to do the "Diva thing". It's something of a Running Gag for a tomboy to say she had no idea how to put on fake eyelashes, do her make-up or sort out hair extensions when she first arrived. The documentary series Breaking Ground shows that female developmental trainees are given classes on how to do their own make-up while on the road.