Catherine "Cat" Storm (Dominique Swain) is a student at an elite New York prep school during The '80s. She wants to get In with the In Crowd and to get with the Troubled, but Cute William Sellers (Brad Renfro). When her best friend, Delilah Milford (Bijou Phillips), is expelled for doing drugs, Cat gets her chance to climb the social ladder.
This film has the examples of:
- Annoying Younger Sibling: Cat's younger brother Pete.
- Bathtub Bonding: Cat and Grace bond this way.
- Be Careful What You Wish For:Cat: [narrating] All I wanted was to impress him, to get his attention.
[wind blows her skirt up right as she's walking by William]
Cat: [narrating] Not exactly what I had in mind.
- The Cameo: Melanie Griffith appears in a brief, walk-on role.
- Every Proper Lady Should Curtsy: The girls all curtsy to their teacher as they enter school. Delilah does it in an exaggerated, mocking way.
- Foreign Exchange Student: Grace is an exchange student from England.
- Forgotten Birthday: Cat's absentee dad forgets to call her on her birthday.
- Girls Have Cooties: After Cat sneezes on Pete's food, he refuses to eat any more on account of it now being covered with her cooties.
- Smart People Speak the Queen's English: Cited by Delilah in reference to Grace: "The only reason those fucking imbeciles let her into our class is because of that accent. They think if you roll your r's you have a higher IQ or something."
- Teacher's Pet: Eloise, who is hated by the other girls for it. Naturally, Cat's mom wishes she'd hang out with Eloise.
- Their First Time: Well, Cat's first time at least. It probably wasn't William's first time.
- Toxic Friend Influence: With the exception of goody-two-shoes Eloise, all the teens in Cat's life encourage her to engage in delinquent behavior, not that she needs too much encouragement in that area.