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Broken Aesop: Any moral the movie is trying to make by having Austin choose Sam in the end (such as looking past wealth and status to love someone for who they really are) is broken by the fact that Sam chooses Austin. Aside from being cute and rich, he has few redeeming qualities. He starts out the movie cheating on his girlfriend with an innocent girl, stalks his "Princeton-Girl" throughout, and wants nothing to do with Sam when he learns she is a waitress. Sam still chooses him over Terry or Carter, who actually like her for who she is.
Another one of the movie's morals is that if you are in an abusive family situation, all you need to do is stick up for yourself and everything will get better. Not only is that full of horrible, horrible Unfortunate Implications, if it was not for the fact that Rhonda was willing to adopt her, Sam would have just made things worse for herself by telling her stepfamily off in the end.
Double Standard: Sam rejecting/being embarassed by Terry because he is a "loser" during the dance is played for laughs. Austin rejecting Sam for being a "loser" is played out as cruel and wrong, though it is not like Shelby publicly mocking Sam made it any harder to be cruel.
Sam confronts Austin in the locker room when the football team is getting ready for the game. Some of the guys are half-naked and at least three of them are only wearing towels (two of which throw it on when they see Sam). Since Sam is a girl it is seen as harmless but imagine the audience reaction to this scene had Sam been a boy walking in a locker room full of half-naked girls.
Hollywood Homely: It's Hilary Duff in a baseball cap! It's hard to believe that Hilary Duff would be considered a "loser" in this at all.
Not really. The only person who ever says she's unattractive is Fiona, who is implied to be jealous of her. That aside, its remarked on about how pretty Sam is by (at least) Carter and Terry, when she's dressed normally. She wears a baseball cap because shes a tomboy who likes baseball.
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