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Sam Montgomery

  • All of the Other Reindeer: It is unclear why, but the whole school seems to dislike her. During the pep-rally scene, everyone joins in chanting "Diner Girl" (Shelby's cruel nickname for her) at Sam
    • ...and, in case you were wondering if they were just playing along with Shelby's little skit, there is a later scene with people laughing and pointing at Sam in the hallway, while she's crying...
    • It's kind of implied that they don't like her because she works in an 'uncool' job. It's not actually that uncommon for kids who are better off to mock and belittle kids who have to work for a living.
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  • Cinderella Circumstances: She is not exactly made into the household drudge, but Fiona does extort the money she makes as a waitress, and makes her work extra hours than Child Labor Laws allow.
  • Cool Loser
  • Hair of Gold, Heart of Gold
  • Only Known by Their Nickname: Not to the audience, but Austin only knows her as "Princeton Girl" and "Cinderella," and the popular kids call her "Diner Girl"
  • Punny Name: Her name is likely a reference to Bewitched, whose main character Samantha, was played by Elizabeth Montgomery.
  • Service Sector Stereotypes: Poor, poor "Diner Girl." Somewhat justified in that her stepmother is taking advantage of the situation.
  • Tomboy with a Girly Streak: Being raised by a single father, Sam grows up knowing more about sports than fashion, though this is more of an Informed Ability at best. She has no aversion to wearing a gown for the ball, is initially upset to learn her mystery boy is a jock, and is more interested in academics than sports. She also loves fairy tales.
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  • The Unfavorite

Austin Ames

  • Big Man on Campus
  • Good Adultery, Bad Adultery: He is essentially cheating on Shelby with Sam from the beginning. This is portrayed as a good thing as Shelby is "evil."
  • Jerk Jock: Played with. He tries to be the Nice Guy and the movie expects us to sympathize with him. He also wants to recreate himself as a writer. On the other hand, he cheats on his girlfriend, practically stalks Sam, rejects her for being a waitress, and makes no effort to stick up for her to Shelby. He does not even appear to help Sam reclaim her inheritance back at the end. It's kind of a Broken Aesop 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. Sam certainly believes this, as why else would she tell him that she was not going to wait for him anymore. For what it's worth, he never goes back to Shelby.
  • Nice Guy: He actively tries to be this, but has issues.
  • Prince Charming Wannabe

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Carter Ferral

Fiona Montgomery

  • Bitch in Sheep's Clothing: Not to the viewer, but it is implied she gets away with exploiting her stepdaughter because she is merely helping her to raise money for Princeton. Little does Sam know that Fiona has no intention of getting rid of her unpaid employee.
  • Conspicuous Consumption: How the hell she is able to flaunt so much is never explained when she would logically have as much as Sam's father, but with even more dependents. Of course, she is at least saving money by extorting Sam, and is probably mooching off her husband's insurance (though this is never mentioned.)
  • Gold Digger
  • Fostering for Profit: Unusually, her victim, Sam, is her stepdaughter rather than a foster-child, but the trope still applies, as she extorts the money Sam makes at the diner for herself. To make matters worse, she also stole Sam's inheritance. Sam could have saved herself years of abuse and humiliation if she just looked in her old storybook.
    • Fortunately, she and her daughters are forced to work off every last cent they took from Sam, including the money Sam earned for them as a waitress.
  • Laughably Evil: Occasionally
  • Make-Up Is Evil: Exaggerated in that she is also obsessed with plastic surgery.
  • Small Name, Big Ego: Somehow owning a diner makes her comparable to Jennifer Lopez.
  • Wicked Stepmother

Brianna & Gabriella

  • Beauty = Goodness: They might just be awkward in appearance, but are truly ugly on the inside.
  • Color-Coded for Your Convenience: They usually wear pink and green, though not consistently, as a reference to the Disney version of the story.
  • Fat and Skinny: Gabriella's fat to Brianna's skinny (In fact, Andrea Avery was instructed to become Hollywood Pudgy in order to invoke the trope).
  • Gasshole: Brianna. As if farting (while in the pool) in her sister's general direction wasn't enough, during the "race" back to the diner, she says (out loud, and in a cat costume, no less) that she needs the "litter box".
  • Little Big Sister: Gabriella is the older of the two by a minute and twenty-six seconds. She never let Brianna forget it.
  • Meaningful Name: Their names are a play on Anastasia and Drizella.
  • Slapstick Knows No Gender: Most of their scenes with each other, especially during the carwash waxing.
  • Spoiled Brat: Both; their spending bites them on the ass when they are forced to pay off their debts for the money they stole from Sam.
  • Those Two Guys: They practically don't do anything until three-quarters into the movie.
  • Too Dumb to Live: Brianna, who even forces Sam to do her homework for her. Gabriella is a bit craftier.
  • Wounded Gazelle Gambit: They lie to Shelby that Sam set up the whole "Cinderella" game in an attempt to hurt her, and add on that they only waited to tell her because she threatened them.

Shelby Cummings

  • Absurdly Powerful Student Council: How the hell does she go unpunished for the pep-rally scene? Seriously, the faculty are visually mortified at what she did to Sam, but they seem to have forgotten they have the power to punish her.
  • Alpha Bitch: She not only mocks and belittles Sam for presumably years, she seems to have turned the whole school against "Diner Girl."
  • Beauty Is Bad
  • Betty and Veronica: The Veronica to Sam's Betty, though it turns out that Sam is likely richer than her, as well as to Astrid.
  • Book Dumb: She thinks that The Three Musketeers is just a candy bar and cheats off of Carter on tests.
  • Evil Counterpart: To Sam.
  • Evil Is Petty: Let's make fun of the girl who has to work for a living! Borders on Fridge Horror when you realize she does not have a problem with Austin being a gas-station attendant (who like Sam, works for his family's business, they are just take advantage of the situation like Sam); when you think about it, she essentially tortures Sam for being an abuse victim.
  • Expy: Being a bitchy blonde who tortures Sam, she is practically a teenage version of Fiona. The movie highlights this by having her be followed around with a red-haired and a brunette lackey.
    • She gets an expy herself in Natalia in Another Cinderella Story.
    • There is also Sonia in the Bollywood remake.
    • There is also Tina in the Italian remake.
      • The idea of giving the prince an evil fiancee seems to have become more popular in recent literary Cinderella retellings. Queen Levana in The Lunar Chronicles or Lady Rainhilda in The Captive Maiden seem to be based on her, especially the latter.
  • Hate Sink: She’s needlessly cruel to Sam and the pep-rally scene will surely get her underneath your skin.
  • Karma Houdini: She goes completely unpunished for torturing and humiliating Sam.
    • Technically, she does lose her rich boyfriend to Sam, and he ends up rejecting her in public, but he intended to do this since the beginning. Carter does the same in the epilogue, but once again it is completely unrelated to her abuse of Sam and only because she rejected him earlier.
  • Kick the Dog: If her rejecting Carter was not enough for you, the pep-rally scene kills what little sympathy you might have for her.
  • Popular Is Dumb: Has to cheat off a "geek" to pass tests, only thinks that The Three Musketeers are chocolate, and doesn't even know what a foreign word for "goodbye" means.
    • To top it off, she and her posse were stupid enough to even believe the lies that the stepsisters told her about Sam wanting to steal away Austin.
  • Rich Bitch: Probably, though the movie never actually mentions that she has money except in a deleted scene, but this is presumably why she looks down on Sam, who was to work for her keep. It is also possible, however, that she is merely a Gold Digger, as she is clearly aware of Austin's money and status.
  • Took a Level in Jerkass: While she is bully from her first appearance, the movie sets her up for a Heel–Face Turn when she shows interest in Carter. She later snobbily rejects him in public when she realizes he is an outcast boy, and when she realizes Sam is "Cinderella," she publicly humiliates her at the pep-rally scene.
  • Ungrateful Bitch: To Carter. He is probably the first guy to ever treat her like a lady, but later wants nothing to do with an outcast like him. After Austin finally leaves her for Sam, Shelby makes another pass at Carter (just because he's moderately famous now), who in turn leaves her for Astrid.
  • Villain with Good Publicity: The pep-rally scene gives shades of this.
    • It may have not lasted. The people cheering for Carter at the end might also be cheering that that he rejected her.
  • Villainesses Want Heroes: Technically subverted in that Austin started out as her boyfriend, though this is partially played straight in that she bullied Sam before she became her rival to Austin.
  • Woman Scorned: Though she victimizes Sam more than her ex, Austin, she exposes Sam as "Cinderella" during a cruel pep-rally skit.

Caitlyn & Madison

  • All There In The Credits: Caitlyn's name is never spoken onscreen in the movie itself.
  • Aristocrats Are Evil: Symbolically; they are Shelby's "ladies-in-waiting."
  • Beauty Is Bad: Like Shelby, they are as pretty on the outside as they are ugly on the inside.
  • Black Best Friend: Madison is this to Shelby.
  • Even Evil Has Standards: They never try to trick Austin into thinking they are "Cinderella," though this is probably more out of a fear of Shelby than anything.
    • Of course, he probably already knows it is not one of them.
  • Expy: They seem to be extensions of the "evil sisters." They have a similar color scheme to them.
  • Green-Eyed Monster: Lampshaded by Shelby when Madison tells her to quit ranting about the guy (Carter) who saved her during the costume party.
    Shelby: "Madison, I think there's a green monster on your back called 'Mr. Jealousy'!"
  • Karma Houdini: They gleefully help Shelby torture and humiliate poor Sam, as if she did not have enough problems, and Carter throughout the movie. The closest they get to a comeuppance is when Carter rejects the three of them when Shelby makes an unsuccessful pass at them. It is possible that they were also trying to flirt with him, or that the whole thing was a last-ditch attempt to save face.
  • Rich Bitch: Similar to Shelby, this is probably the case, but this is unconfirmed in the final movie.
  • Those Two Guys

Rhonda

  • Black Best Friend
  • Dark and Troubled Past: She got into fights in school and left some guy at the altar. Fortunately, she kept the dress...
  • The Dog Bites Back: She ends up Fiona's supervisor.
  • Fairy Godmother
  • Girl Friday: To both Sam and her father...
  • Karmic Jackpot: Sam, after discovering her father's will, makes Rhonda the diner's co-owner, and keeps an eye on her former Bad Boss Fiona.
  • Parental Substitute: To Sam. Fittingly, she adopts Sam by the end.
  • Sassy Black Woman: She is usually a friendly, caring person, but she will get sassy if you deserve it. Partially subverted in that she puts up with Fiona for Sam's abuse.
  • Screw the Rules, I Have Connections!: She is able to get away with going against Fiona's abuse because she practically runs the place, and especially brings in the clientele. She manages to get the entire diner to walk out on Fiona in Sam's defense towards the end.
  • Service Sector Stereotypes: Played with. Being a waitress is actually portrayed as a decent job for Rhonda when she worked for Sam's father, and only became demeaning when Fiona took over. Played straight in that her happy ending is being promoted to "co-owner."
  • Team Mom
  • You Are Not Alone: After losing everything towards the climax, Rhonda assures Sam this is the case.

Hal Montgomery

  • Deceased Parents Are the Best: Though he was stupid enough to marry Fiona, he at least had the sense to leave everything to Sam.
  • Uncle Pennybags: Probably; the movie never mentions how financially well-off he was, but considering how much Fiona flaunts his wealth after his death, he probably was not doing so bad.
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