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* JerkJock: Played with. He tries to be the NiceGuy and the movie expects us to sympathize with him. He is also tired of being part of the popular crowd and having to meet their expectations and his father's, wanting to recreate himself as a writer. On the other hand, he cheats on his girlfriend, practically stalks Sam, rejects her for being a waitress, makes no effort to stick up for her to Shelby, and appear to not care about Sam's well being in the first place. He does not even appear to help Sam [[spoiler: reclaim her inheritance back at the end]], though it's possible he might've been hashing out things with his father at the same time. It's kind of a BrokenAesop that his only redeeming characteristics are that he is rich and pretty. To his credit, it is implied that he never actually rejected Sam, he was just unsure what to do in the situation, and was possibly hurt by her not coming forward about her true identity when she had the chance (though this is still no excuse for not standing up for her). Sam certainly believes this, as why else would she tell him [[spoiler: that she was not going to wait for him anymore.]] For what it's worth, he never goes back to Shelby and he doesn't even call her out for all the horrid things she did to Sam, though in this case, he probably figured it wouldn't have made a difference since Shelby was clearly to stuck in her snobbish ways to change.
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* JerkJock: Played with. He tries to be the NiceGuy and the movie expects us to sympathize with him. He is also tired of being part of the popular crowd and having to meet their expectations and his father's, wanting to recreate himself as a writer. On the other hand, he cheats on his girlfriend, practically stalks Sam, rejects her for being a waitress, makes no effort to stick up for her to Shelby, and appear to not care about Sam's well being in the first place. He does not even appear to help Sam [[spoiler: reclaim her inheritance back at the end]], though it's possible he might've been hashing out things with his father at the same time. It's kind of a BrokenAesop that his only redeeming characteristics are that he is rich and pretty. To his credit, it is implied that he never actually rejected Sam, he was just unsure what to do in the situation, and was possibly hurt by her not coming forward about her true identity when she had the chance (though this is still no excuse for not standing up for her). Sam certainly believes this, as why else would she tell him [[spoiler: that she was not going to wait for him anymore.]] For what it's worth, he never goes back to Shelby and he doesn't even call her out for all the horrid things she did to Sam, though in this case, he probably figured it wouldn't have made a difference since Shelby was clearly to too stuck in her snobbish ways to change.
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* FairyGodmother: She acts as a MamaBear figure to Sam and helps her sneak to the school prom, even providing a gown.
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->'''Portrayed by:''' Creator/HilaryDuff
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->'''Portrayed by:''' Creator/HilaryDuffCreator/HilaryDuff(Aged 16)
Hannah Robinson(Aged 10)
Hannah Robinson(Aged 10)
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* HairOfGoldHeartOfGold: She's a blondie (due to being played by Hilary Duff, who is blonde, albeit [[DyeHard naturally brunette]]) and has a sweet personality.
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* HairOfGoldHeartOfGold: She's a blondie (due to being played by Hilary Duff, Duff and Hannah Robinson, who is are blonde, albeit [[DyeHard naturally brunette]]) and has a sweet personality.
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[[folder:Hal Montgomery]]
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* TheDogBitesBack: [[spoiler: Once she finds her dad’s will, she finds out she’s the sole heir to his properties and wealth. The first thing she does is sell her abusive stepfamily’s cars to help pay for her new life at Princeton, leading to the cops to chase Fiona around the yard since due to her witness statement of her late husband’s will. She also forces her stepsisters to dig into garbage to find her acceptance letter. Rather than go to prison, Fiona and her daughters agree to work off their debt at the diner to pay back all the money they stole from her inheritance.]]
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* TheDogBitesBack: [[spoiler: Once she Sam finds her dad’s will, she finds out she’s the sole heir to his properties and wealth. The first thing she does is sell her abusive stepfamily’s cars to help pay for her new life at Princeton, leading to the cops to chase Fiona around the yard since due to her witness statement of her late husband’s will.will and depriving Sam of all of her father’s belongings. She also forces her stepsisters to dig into garbage to find her acceptance letter. Rather than go to prison, Fiona and her daughters agree to work off their debt at the diner to pay back all the money they stole from her inheritance.]]
