When a girl (or, in some cases, a guy), regardless of her actual attractiveness, believes herself to be unattractive. Many such girls are lacking in conventional attractiveness, but it's rare for them to be ugly. Often the complaint of a girl who believes herself to be 'plain' or 'boring' compared to model-level-gorgeous believe that she's simply not attractive at all for whatever reason.
An Amazonian Beauty may believe herself to be unattractive because she's suffered from No Guy Wants an Amazon, and she doesn't realize that she's hot. On a similar note, a Bokukko or Shorttank may believe that she's too masculine because she's always been One of the Boys. A Pettanko may believe this as well, due to A-Cup Angst.
A girl who is above the so-called 'ideal weight' may believe herself to be fat and unattractive because of it, even if she is a Big Beautiful Woman or simple Hollywood Pudgy.
A Meganekko may believe that The Glasses Gotta Go, even if they are her true charm, or may believe that even without her glasses, she's plain and/or ugly.
A Wrench Wench may believe that wearing coveralls and being covered in grease all the time means she's got no feminine appeal even though many guys (and girls) are really into that kind of thing.
Sometimes she might be a standard beauty, but feels unattractive because she's the wrong kind of beautiful. A girl with Raven Hair, Ivory Skin who's an absolute knockout to anyone with eyes might still feel she's unattractive because she's told the "ideal" is blue-eyed blonde. This one is especially common in the U.S.; the standard of beauty is an ideal that could be considered Northern European (blonde hair, blue eyes, tan complexion,) which leaves a lot of girls in minority groups feeling this way (Cher has said in the past that she grew up feeling like she could never be beautiful because she wasn't blonde.)
This is often the basis behind a Beautiful All Along or She Cleans Up Nicely event; when a character who is seen (rightly or wrongly) as unattractive is gussied up and made the Belle of the Ball. However, the main issue at hand is not how other characters see her, but the fact that she sees herself as unattractive. If the girl can realize her worth and attractiveness without a makeover, so much the better.
The Trope Namer is Thelma Possum from Nip And Tuck, a webcomic by RH Junior. It takes a huge effort on the part of her beau and friends to convince her that she's beautiful and worth knowing.
Sub-Trope of Obliviously Beautiful where an attractive character is simply unaware of their beauty. Related to Hollywood Homely, where we are informed that the girl is unattractive or ugly, and everyone in the show seems to believe it, but to us she seems quite pretty. With Suetiful All Along, the author insists the character isn't pretty at the outset, then lavishes complimentary descriptions on her the rest of the time. A girl who is fishing for compliments may pretend to feel this way, but she really doesn't. This can be Truth in Television, if the girl in question has a poor self-image and/or unrealistic ideas of what constitutes beauty.
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Anime and Manga
Played straight in The Wallflower, where Sunako believes she is ugly simply because a boy she liked told her she was. Cue the whole series revolving around her "ugliness", even though she's a bishoujo.
Male example: Natsume Takashi from Natsume Yuujinchou has been used to being ostracized or bullied most of his life because people considered him a Creepy Child. Thus, he's a bit surprised to find out that many of the kids at his high school consider him quite attractive
Natsume: ...Good looks? Nobody's ever said that to me before.
Yura of Honey Hunt believes herself to be plain. This isn't helped by how other people tell her that compared to her beautiful and successful mother she's quite plain. However, once she loses the glasses and fixes her hair she can actually be quite good looking.
In Naruto, Kushina says this word by word when we finally meet her. Even if she's, well, dead. It Makes Sense in Context. She even apologizes for giving Naruto her face.
In Axis Powers Hetalia, Vietnam considers herself to be plain and not photogenic. Taiwan tells her she's a cutie, though.
Belgium also considers herself as such, but doesn't make a big fuss of it. In her own words:
Belgium: "With all these strong guys around me, I may appear a bit plain, but I'm doing my best"
The "strong guys" bit implies that she thinks she doesn't stand out as much or isn't as powerful/influential as her neighbours, rather than lack of physical attractiveness.
Sakurako Sanjou from Hana Yori Dango gets extensive plastic surgery just because other children, especial importance placed on Tsukasa, called her ugly as a kid. In the Japanese drama, the girl playing her is not at all ugly.At age sixteen, people.
The Demon Queen in Maoyuu Maou Yuusha is a curvaceous, busty, stunning redhead that believes she's "wasted away" because she has devoted too many decades to her field of expertise (Economical Science),
The title character from Empowered tries to believe she's beautiful, but rarely manages it, despite being drop-dead gorgeous even by superheroine standards. Sistah Spooky's constant digs do nothing to help.
The Hunger Games fanfiction Some Semblance of Meaning has heroine Vale Whitaker being surprised at the sight of her reflection after her makeover because she "had never felt even remotely pretty in her entire life.... She didn't have crowds of friends, and boys didn't even seem to realize that she was alive. So surely she couldn't have been even the slightest bit pretty. Surely someone (besides her parents, who were required to think so) would have told her by now if she was." It seems that not everyone agrees with her assessment, however—or at least, Obsidian doesn't.
Fiona of Shrek was cursed to become an ogress and later becomes one permanently after sharing a True Love's Kiss with Shrek. At the end of the first movie she tells Shrek "I don't understand. I'm supposed to be beautiful." Shrek responds with "But you are beautiful." And indeed, she's still pretty for a Cute Monster Girl.
Tanya says this of herself in An American Tail: Fievel Goes West. Ms. Kitty, (as well as most fans of the movie) begs to differ, and gives her a makeover. At the end of the movie though she gets over it, and washes her makeup off.
Subverted in Shallow Hal, when Hal (Jack Black) believes that his "slender" love-interest (Gwyneth Paltrow) has been abused into simply thinking she's not beautiful — when the fact is that she weighs 300 lbs., but he's simply been hypnotized into thinking that she looks like Gwyneth Paltrow.
Celine in Before Sunrise. Actually, the trailer for Before Midnight and a scene in Before Sunset. In the latter, she asks how she's different, and Jesse responds that she's thinner. She then says she was a "fat French girl." And in the trailer for the former, she describes herself as a "fat-ass, middle-aged mom losing her hair." This is Julie Delpy !
Sara Crewe in A Little Princess thinks she must not be pretty because she doesn't mesh with the beauty standards of late-nineteenth-century England, being small, skinny, black-haired, tanned, and green-eyed, but the author tells us that she's definitely pretty in her own way.
In Howls Moving Castle, it's more of a matter that Sophie lacked confidence and self-esteem to see herself as pretty and sees herself as plain and doomed to a boring life.
And Wrong Genre Saviness: Sophie is the eldest of three sisters, and is the protagonist of a story - she just assumes it's a classic fairy tale instead of modern fantasy.
Lee in Prep; "There were other things a guy could think I was, and he wouldn't be entirely wrong - nice, or loyal, or maybe interesting. Not that I was always any of those thing, but in certain situations, it was conceivable. But to be seen as pretty was to be fundamentally misunderstood. First of all, I wasn't pretty, and on top of that I didn't take care of myself like a pretty girl did; I wasn't even one of the unpretty girls who passes as pretty through effort and association. If a guy believed my value to lie in my looks, it meant either that he'd somehow been mislead and would eventually be disappointed, or that he had very low standards.”
Anne Shirley, of Anne of Green Gables. While in the first book she genuinely is as plain as she believes herself to be, as she matures she takes on a kind of attractiveness that's just unconventional for her time period. The fact that she's a Fiery Redhead in a time period where red hair was deemed horribly unattractive does give her some grounds for believing this even as an adult, however untrue it really is. It's implied that sympathetic people are the kind who will find her pretty, while the jerks think her plain.
Parodied in Discworld book Thud! . Where the human-despite-all-appearances-to-the-contrary-Nobby Nobbs starts dating a beautiful strip dancer, Tawneee, no one can believe it. Apparently, she thinks herself ugly. Why? Because every other guy assumed that she was out of their league and never approached her, leading her to believe she was unattractive.
Friday, the protagonist in the Robert A. Heinlein novel Friday, suffers from this. When "Boss" Baldwin informs her that he thinks she is beautiful, she thinks to herself, "Really, Boss, I do own a mirror, y'know."
A curious example appears in Kit Williams' well-known puzzle book Masquerade. The Sun is in love with the Moon but daren't speak to her. This is because people always screw their faces up whenever they look at him, which leads him to think he must be very ugly.
In an unusual variant young Fawn Bluefield from The Sharing Knife frequently berates herself for her stupidity, to the point where Dag Redwing (who thinks she has a mind like a steel trap, and considers it one of her most attractive features) noted early on:
"You use that word a lot. Makes me wonder who used to whip you with it."
A character in Sidney Sheldon's Master of the Game describes herself as "not pretty but interesting-looking," despite being stunningly beautiful in the eyes of all the other characters.
Live Action Television
In Dollhouse with Bennet Halverson concerned that Topher had just tried to taze her with a device that only works on Dolls. She has a hard time believing this because Dolls are beautif... oh.
An early Twilight Zone episode has a young lady whose head is swathed in bandages as the plastic surgeon laments that he was unable to do much for her. They remove the bandages to reveal she has a lovely face and is, in fact, quite beautiful. As the doctor and the nurses all gasp with dismay and disgust, the point of view pulls back to reveal they are all horribly disfigured by our standards, with ugly pig-snoutish noses. By their standards, she was the horribly disfigured one. The young girl sees her reflection in a mirror and bursts into tears at seeing herself as so ugly.
Subverted in a Saturday Night Live skit when Pamala Anderson cohosted. The scene played out as above until the young girl (played by Ms Anderson) looked at herself in the mirror. She jumped up and exclaimed in delight, "Hey, I'm Hot. I'm the hottest Chick on this planet" and ran from the room.
When Bridget of 8 Simple Rules was playing Anne Frank in a school play, one of her lines was "I know I'm not very pretty". She bursts out laughing when she says this in rehearsals since she knows she is indeed stunning.
In some episodes of 3rd Rock from the Sun, Sally believes herself to be unattractive, despite her being a leggy, big-busted blonde. Similarly, she thinks portly Officer Don is incredibly attractive. This is because the aliens don't understand human beauty standards.
Invoked and averted in the Girls episode "One Man's Trash" with Hannah and her fling, Joshua, Josh. He tells her that she's beautiful, she skeptically replies "You really think so?", then he asks if she believes the opposite to which she replies: "I do. It's just not always the feedback that I've been given." In short, she gets that she isn't model-gorgeous but that she is at least decent looking.
The waitress in the Harry Chapin song "A Better Place To Be": "I wish that I was beautiful, or you were halfway blind..."
Averted in Katawa Shoujo. The original illustration has Hanako reacting this way to a Love Confession; in the finished game, though, this doesn't happen. She's self-conscious about her scars, but she never directly calls herself ugly or unattractive.
Saber from Fate/stay night has serious problems comprehending that anyone could be attracted to her and when finally it gets through to her that Shirou is really interested in her she develops a inferiority complex. Somewhat justified by her past in which she was posing as a man (and a king) and so no other man ever made a move on her.
Jadis from the Whateley Universe believes herself to be unattractive. She's plain at worst, but most of her issues come from being in a school full of Exemplars, and while she's been classified as an Exemplar, she hasn't got the looks to go with it.
Iriana of Ilivais X is a little in the Uncanny Valley, but she believes that she's an undesirable freak and not even worth being called human. However, every single one of her teammates thinks she's VERY cute, Mille in particular consistently fantasizing about her.
Marigold Farmer from Questionable Content believes herself to be fat and ugly. While she does have bad skin and poor hygiene, she's actually considered rather cute, and has a not-terrible figure, being Hollywood Pudgy.
Art Evolution eventually gives Marigold a figure similar to Faye's, to the point that Faye lends her a swimsuit... and grudgingly admits that "she looks better in it than I do." Marigold's opinion?
Marten & Steve: Daaaaaaaaaaaaaang!
Marigold: STOP DANG-ING AT ME.
Liri from The Challenges of Zona believes she is ugly and unattractive, because she is a giantess and has been reviled by humans her whole life. This persists even after she met and fell in love with another giant, Keltan, leading to the two of them having Innocent Cohabitation until Zona, the main character, convinces her otherwise and tells her about sex.
Played for Drama in an episode of Batman: The Animated Series. Batman and Batgirl have managed to corner a masked criminal who was attacking young models. The criminal herself was a model, but was forced out of the industry for being "too ugly." The police unmask her... and she's just as beautiful as the other models she's been targeting.
Batman: She can't see that anymore. All she sees are the flaws.
Audrey Hepburn thought she wasn't very attractive. Allegedly, she once said: "I never thought I'd land in pictures with a face like mine".
And of course, Page Image, Penelope Cruz doesn't think she's beautiful. Proving once and for all: Beauty is in the eye of the beholder.
Scarlett Johansson once described her face as "stuck on there and there's nothing I can do about it."
Nicole Scherzinger went through a bad bout of low self-esteem and eating disorders because of this. She specifically mentioned that she was born in Hawaii but moved to Kentucky, she always felt out of place as a Polynesian girl surrounded by blonde-haired, blue-eyed Southern Belles.
This article gives some insight into why women and girls hardly say the opposite.
Doug Walker apologized for having to show his "mug" every day on the site for two months in "The Last Airbender Vlogs". Big change from the guy who bragged about being a Mr. Fanservice to both genders.
Jessica Alba: "My breasts are saggy, I’ve got cellulite, my hips are bigger ," Alba said. "Every actress out there is more beautiful than me".