"They were five total strangers, with nothing in common, meeting for the first time. A brain, a beauty, a jock, a rebel and a recluse. Before the day was over, they broke the rules. Bared their souls and touched each other in a way they never dreamed possible."

"They only met once, but it changed their lives forever."

"Yeah, I got a question. Does Barry Manilow know that you raid his wardrobe?"

"[to Claire] You know how you said before that your parents use you to get back at each other? Wouldn't I be outstanding in that capacity?"

"Hey, how come Andrew gets to get up? If he gets up, we'll all get up…it'll be anarchy!'"

"Screws fall out all the time; the world is an imperfect place."

"Chicks cannot hold their smoke, dat's what it is."

"[first lines] Saturday, March 24, 1984. Shermer High School, Shermer, Illinois, 60062. Dear Mr. Vernon, we accept the fact that we had to sacrifice a whole Saturday in detention for whatever it was we did wrong. What we did was wrong. But we think you're crazy to make us write an essay telling you who we think we are. What do you care? And you see us as you want to see us - in the simplest terms, in the most convenient definitions. You see us as a brain, an athlete, a basket case, a princess, and a criminal. Correct? That's the way we saw each other at 7:00 this morning. We were brainwashed."

"I happen to like being adored, thank you."

"You're asking me out? That's so cute! What's your name again?"

"It's not everyday you find a girl who'll flash someone to get you out of detention."

"Gabrielle Union - Chastity, Bianca’s best friend"

"David Leisure - Mr. Chapin"

"Allison Janney - Ms. Perky"

"Daryl "Chili" Mitchell - Mr. Morgan"

"Susan May Pratt - Mandella, Kat’s best friend and Michael’s love interest"

"I hate the way you talk to me, and the way you cut your hair. I hate the way you drive my car, I hate it when you stare. I hate your big, dumb combat boots and the way you read my mind. I hate you so much it makes me sick — It even makes me rhyme. I hate the way you're always right. I hate it when you lie. I hate it when you make me laugh — Even worse when you make me cry. I hate it when you're not around. And the fact that you didn't call. But mostly I hate the way I don't hate you — Not even close, not even a little bit, not even at all."

"David Krumholtz - Michael Eckman, Cameron’s best friend"

"What is it with this chick? She got beer flavored nipples?"

"Andrew Keegan - Joey Donner"

"Larry Miller - Dr. Walter Stratford, Kat & Bianca’s father"

"Larisa Oleynik - Bianca Stratford, Walter’s daughter and Kat’s younger sister"

"Joseph Gordon-Levitt - Cameron James, Bianca's love interest"

"Heath Ledger - Patrick Verona, Kat’s love interest"

"Remove head from sphincter, then drive!"

"No drinking, no drugs, no kissing, no tattoos, no piercings, no ritualistic animal slaughters of any kind. Oh, God, I'm giving them ideas."

"Julia Stiles - Kat Stratford, Walter’s daughter and Bianca’s older sister"

"They're spitefully romantic."

"Romeo, Oh Romeo, Get Out Of My Face."

"I burn, I pine, I perish!"

"How do I loathe thee? Let me count the ways."