Movies where dorky, not-conventionally-attractive girl gets the guy of her dreams? (Spoilers OK)

We’ve all seen this played out in the opposite direction. He’s a nerd, or has no social skills, or he’s not very attractive, etc. He has feelings for a woman who is gorgeous and way out of his league, and it turns out she is charmed by him and they get together. Albert and Allegra in Hitch, Colin and (and possibly Sam and Joanna) in Love Actually, Arthur and Tricia in The Hitchhiker’s Guide to the Galaxy, Bleeker and Juno in Juno, the entire plot of The 40-Year-Old Virgin…I could go on, and TVTropes does.

Is there any movie with the inverse of this cliché? A friend offered My Big Fat Greek Wedding, which is a positive step forward, but as a dorky girl who doesn’t look quite like a supermodel, I would despair if there is only one such movie.

Have you tried taking your glasses off and letting your down? It can work wonders, especially if you shake your head in slow motion.

Well, typically in those movies, the girl is merely Hollywood Homely. Usually after a makeover, it is revealed that she wasBeautiful All Along.

But here are some examples of movies you described:
My Big Fat Greek Weding (Nia Vardalos)
Circle of Friends (Minnie Driver)
Penelope (Christina Ricci)
The House Bunny (Emma Stone)
Miss Congeniality (Sandra Bullock)
The Princess Diaries (Anne Hathaway)
Never Been Kissed (Drew Barrymore)
The Breakfast Club (Ally Sheedy)

Personally, I would love to find a dorky girl who doesn’t look quite like a supermodel.

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Muriel’s Wedding (Toni Collette)

That film is a perfect example of Hollywood’s bizarre idea of “unattractive”. Janeane Garofalo was damned cute in that film - more attractive (to me) than Uma Thurman. Stephen King wrote a review of the terrible movie The Lawnmower Man and said, about the lead character in the film, “In Hollywood movies geeks are never really unsightly. They just have bad haircuts.”

That’s funny, as I said the exact same thing to the young woman that I saw it with (who I was absolutely crazy about, but that’s another story) and she totally refused to believe that I honestly thought that Janeane Garofalo was better looking than Uma Thurman.

I still think that JG is hot, and Uma has never done too much for (or to) me…

Antonia and Jane, a British movie from 1990 which I love and recommend, is exactly the kind of movie you’re descibing. The “homely” girl really is done up to be fairly plain and frumpy. The picture on the movie poster on the page is deceptive; she’s exceedingly plain and awkward in the film, and is contrasted with a gorgeous best friend. I’d forgotten all about this film!

Ugly Betty has gotten the guy numerous times, and while we all know how gorgeous she is in real life, she is no glamour queen on the show (well, much more so this season after her makeover).

What about Georgy Girl?

She’s All That was the stereotype of this genre.

Yeah, but IIRC her personality sucked. I mean assuming she was just like every other character Garofalo plays, she was sarcastic, hostile, and unfriendly. I thought the whole problem was with her and her inability to accept that some guy might find her attractive even though she wasn’t tall and blonde.

I’d like to see the high school where Romy & Michelle (Lisa Kudrow and Mira Sorvino) were the unpopular dorks.

And Janeane Garofalo plays a homely girl in Romy & Michelle’s High School Reunion who becomes more attractive with age. It’s a very funny movie, by the way, if you can tolerate the exaggerated accents.

Except that she doesn’t get the guy of her dreams at all. Of course, one could argue that she got the woman of her dreams, but that was all subtext.

There’s the cheesy but guilty pleasure film If the Shoe Fits, with Jennifer Grey and Rob Lowe. It’s basically Cinderella, where Jennifer is a geeky shoe designer/doormat who wants a chance to work with obnoxious, egomaniac, fabulously weathy and gorgeous fashion designer Rob Lowe. After politely helping a wacky old woman, who turns out to be a fairy godmother, Jennifer is turned into an alter-ego who’s supposedly drop-dead gorgeous – but only whenever she wears a pair of magic shoes. Rob falls for this alter-ego, and Jennifer starts to get exactly what she wants. Except not, because she realizes that her plain ol’ normal self isn’t good enough for Rob.

Anyway it all works out in the end without a makeover. As I said, it’s a highly cheesy film with an '80s vibe, but it’s still enjoyable because Jennifer/Rob are sweet together.

(I suppose Dirty Dancing kind of works too, but I think Jennifer isn’t really playing a dork… I don’t think she’s labeled unattractive or anything like that in the movie.)

Starring the famously dorky and unattractive Lynn Redgrave. :wink:Still from the movie here.

Lynn is so awesome.

Oh, and I don’t know if Bridget Jones counts–she’s not SO dorky, but I guess she’s meant to be…and Bridget Jones definitely reminds me of Georgy. It feels very much in that vein–larger than average girl choosing between two guys.

In my case, it was strictly physical—I have never found Janeane Garofalo to be funny or engaging, and when I have watched her on talk shows, she comes off as arrogant and projects the vibe of someone who is trying way too hard to be hip.

I still think she is hotter than Uma Thurman though…

I do think that Uma is quite attractive overall, but there are hundreds of women around, (both famous and not) who are better looking than she is, and Janeane Garofalo is certainly one of them.

Ugh. This movie pisses me off, because of how much they changed the ending from the book. In both, Minnie Driver’s character is portrayed as a somewhat shy, too tall, slightly chunky girl who blossoms while dating the guy (was his name Jack? I can’t remember). I’ll put the rest under a spoiler tag, just in case…

The guy ends up cheating on her with her best friend, who seduces him because she’s pregnant with another guy’s kid. The other guy won’t marry her and she won’t get an abortion, being Irish Catholic and all, so she gets Bennie’s boyfriend drunk and sleeps him while Bennie is away helping with the family store after her father’s death. Also, Bennie wouldn’t sleep with him, which was an issue in their relationship. Bennie returns only to have her boyfriend tell her that Nan is pregnant, it’s his kid, and they’re getting married. Eventually Nan’s deception is found out. In the movie, Bennie gets back with him and sleeps with him. In the book, she has enough confidence to tell him to fuck off when he comes crawling back to her, and while she’s horribly broken up about it at first, at the very end she is cool but polite to him at a school bonfire, and ends up starting to flirt with a mutual friend instead. I loved the book, because she really grew up, gained a bunch of confidence, and was able to not be the complete fucking doormat that she turned out to be in the movie. Ugh.

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