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John Tucker
Played by: Jesse Metcalfe
- The Ace: A charming, handsome, popular, talented athlete.
- Aloof Big Brother: To Scott.
- Anti-Villain: Rather sympathetic, despite being such a class A jerk to girls.
- Big Man on Campus: Every embarrassing thing he does becomes an instant trend.Beth: I'd hit him with my car if he wouldn't make body casts a fashion statement.
- Butt-Monkey: The girls put him in some really embarrassing situations.
- The Casanova: He dated three different girls at the same time.
- Humiliation Conga: The whole movie is basically John going through one humiliating moment after another. From being rumored to have herpes, being given estrogen, to being paraded in front of the entire basketball team wearing nothing but panties, John's life just becomes one embarrassing situation a in after another.
- Jerk Jock: While John is not a bully towards anybody, he is still an asshole towards girls that he dates.
- Lady Killer In Love: With Kate. It changes him.
- Not Good with Rejection: He can't resist a woman who plays hard to get.
- Sibling Yin-Yang: John's a big manly-man jock while Scott is the more sensitive nerdy type.
Kate
Played by: Brittany Snow
- All Guys Want Cheerleaders: Invoked Trope, where she joins the cheerleader squad in order to get John's attention as part of the scheme.
- Anti-Hero: Played With. Kate is the film's protagonist, but her goal is to humiliate John by manipulating his emotions. However, she doesn't mean anything cruel by it, and realizes that it's not a good thing to do either.
- Becoming the Mask: Her main arc. She initially gets involved with John as part of the girls’ revenge scheme against him. However, she starts to actually fall in love with him, thus causing her to reconsider her role in the plan. Lampshaded by her mother and Scott.
- Birds of a Feather: With Scott.
- Deadpan Snarker: Her mother's boyfriends seem to bring it out of her.
- Everyone Loves Blondes: Especially if your last name is Tucker.
- Fetishized Abuser: Invoked by her in order to seduce John.
- Friendless Background: Before Heather, Beth, and Carrie, Kate never had any other friends due to moving around constantly.
- I Just Want to Have Friends: Thanks to said Friendless Background.
- The Ingenue: A virginal cutie.
- Intentional Heartbreaker: In an attempt to get revenge on John, the others convince Kate to break his heart and teach him a lesson. It doesn't go well.
- Naïve Newcomer: The new girl in school.
- Never My Fault: Kate blames her mother's poor dating choices on why she's turning into an Alpha Bitch.
- It's All My Fault: However, she does learn the errors of her ways and sets things straight after John's party.
- Nice Girl: Kate is usually this.
- Sugar-and-Ice Personality: Invokes this in order to win over John.
Carrie
Played by: Arielle Kebbel
- Academic Alpha Bitch: Carrie seems to be rather popular, acting as a rival to Heather. However, unlike Heather, she’s smart, part of many extracurricular activities and cares a lot about her education.
- Extracurricular Enthusiast: she is the head of at least four after-school clubs.
- Go-Getter Girl: Of the Academic Alpha Bitch variation.
- Jerk with a Heart of Gold: Like the other two girls - her regular act is pretty bitchy, but she is actually pretty nice.
- School Newspaper News Hound: She takes the school TV station very seriously.
- Student Council President: See Extracurricular Enthusiast.
- Woman Scorned: Her motive to destroy John.
Beth
Played by: Sophia Bush
- Ambiguously Bi: She comments on Kate's mom's hotness and she kisses Kate (albeit for practice).
- Brainy Brunette: Deeply subverted.
- Butt-Monkey: She still loses her skirt even after she doesn't date John.
- The Ditz: She means well, but her behavior is usually bordering on the silly.
- Granola Girl: She is made of this trope - a militant vegan who gets her yearbook pictures printed on recycled paper. (Sophia Bush is similar in Real Life.)
- Jerk with a Heart of Gold: Downplayed, in comparison to Carrie or Heather, but it seems she is pretty mean. While befriending the others, she is revealed to actually be rather kindhearted.
- Really Gets Around: Apparently, it's a vegan teen activist thing. Frequently lampshaded.Carrie: Beth is still in the car!Heather: Slut in truck! I repeat, slut in truck!
- Soapbox Sadie:(shouts at the basketball game) "Kill the Bobcats!" (turns back to her vegan friends)' "Not the real bobcats - they're endangered!"
- Woman Scorned: Her motive to destroy John.
Heather
Played by: Ashanti
- Alpha Bitch: She is the head cheerleader. Downplayed, probably to set up the Jerk with a Heart of Gold Character Development.
- Lovable Alpha Bitch: Following said Character Development.
- Cruel Cheerleader: Downplayed. While clearly rude and self-centered, she is far from evil.
- Jerk with a Heart of Gold: Heather becomes this in the climax.
- Really Gets Around: Not as much as Beth, but it's implied.Beth: It's not like everyone doesn't know that Little Miss Cheerleader brings it on.
- Sassy Black Woman: She is all about the attitude.
- Woman Scorned: Her motive to destroy John.
Scott
Played by: Penn Badgley
- Birds of a Feather: With Kate.
- The Everyman: He doesn't have anything special going on for him - especially in comparison to his brother.
- In-Universe Nickname: The Other Tucker.
- The Klutz: So klutzy, he is a threat to his lab-partner's safety.
- Nice Guy
- Sibling Yin-Yang: John's a manly-man jock while Scott's the more sensitive nerdy type.
- Sir Not-Appearing-in-This-Trailer: Very untypical, given his status as a Love Interest.
- The Unfavorite: Implied, because he mentions that his mom told him that he is "special on the inside."
- What the Hell, Hero?: Gives this speech to Kate after realizing that she and the girls have been scheming against his brother.
Lori
Played by: Jenny McCarthy
- Even the Girls Want Her: Beth seems to be really into her.
- Good Parents: Kate's single mother is a good mother towards her, offering her advice for everything.
- Looking for Love in All the Wrong Places: Kate took to calling Lori's boyfriends "Skip" because they would all end up skipping out on her.
- Parents as People: While Kate's mom is a good mother towards Kate, she still has some flaws. It's shown that Kate's mom's tendency to look for love in the wrong places seems to have a negative effect on Kate regarding her attitude towards certain men.
- Plucky Girl: No matter how many times she gets her heart broken, she puts herself out there again.
- Really Gets Around: She has enough hookups with enough bums to make a montage out of it.
- Stacy's Mom: Apparently, she is so hot it stood in Kate's way to make friends. Even Beth comments on her hotness.