- Directed by Will Gluck. Written by Bert V. Royal.
Olive Penderghast 
- Let the record show that I, Olive Penderghast, being of sound mind and below average breast-size, swear to tell the truth, the whole truth, and nothing but the truth... starting now.
- [to Marianne] We've had nine classes together since Kindergarten...ten if you count Religion of Other Cultures, which you didn't because you called it science fiction and refused to go.
- [to Brandon as she removes her panties] Relax. Jesus. What is with you gays? Are you really that repulsed by lady parts? What do you think I have down there? A gnome?
- [to Evan] I want a one hundred dollar gift card deposited into my locker by noon tomorrow. Preferably to The Gap, but I'd also take Amazon.com, or Office Max. Actually make it Office Max – I have my eye on a label maker. We did not have sex. I let you fondle my chest, and it was a glorious moment for you. Unmatched by anything you have heretofore experienced...including cake.
- The rumors of my promiscuity have been greatly exaggerated.
- That's the one thing that trumps religion...capitalism.
- "A" is for awesome!
- Whatever happened to chivalry? Does it only exist in 80's movies? I want John Cusack holding a boombox outside my window. I wanna ride off on a lawnmower with Patrick Dempsey. I want Jake from Sixteen Candles waiting outside the church for me. I want Judd Nelson thrusting his fist into the air because he knows he got me. Just once I want my life to be like an 80's movie, preferably one with a really awesome musical number for no apparent reason. But no, no, John Hughes did not direct my life.
- [about Todd] I think I'll lose my virginity to him. Maybe in five minutes, maybe tonight, maybe sixth months from now, or maybe on our wedding night. But you know what? It's nobody's God damned business.
- Well if that's our magical love connection, I should just date the whole school.
- [to Olive] You've made your bed...I just hope for your sake, you've cleaned the sheets.
- Jesus tells us to love everyone, even the whores and the homosexuals. But it's so hard, it's so hard because they keep doing it, over and over again.
- That's not something you need to advertise, Kurt!
- Principal Gibbons: This is public school. If I can keep the girls off the pole and the boys off the pipe, I get a bonus.
- Brandon: Oh, well.... Let's just say I'm gonna be walking funny tomorrow! *silence* I'M DRUNK. WHAT'S UP, BITCHES?
- Mr. Griffith: [to Olive] I don't know what your generation's fascination is with documenting your every thought...but I can assure you, they're not all diamonds. "Roman is having an OK day, and bought a Coke Zero at the gas station. Raise the roof." Who gives a rat's ass?
- Mrs. Griffith: I'm the guidance counselor. I should know all the students, especially the ones that dress like prostitutes.
- Marianne: There's a higher power that will judge you for your indecency.
- Olive: Tom Cruise?
- Nina: Perhaps you should embroider a red "A" on your wardrobe, you abominable tramp.
- Olive: Perhaps you should get a wardrobe you abominable twat.
- Marianne: (stapling papers)Looks like someone's on a downward spiral.
- Olive: Looks like someone's practicing the mundane activity she'll be saddled with the rest of her pathetic life.
- Rhiannon: You're being pretty cavalier about this. Aren't you supposed to be eternally in love with him and shit?
- Olive: Yes... I believe so, if I was the Gossip Girl in Sweet Valley of the Traveling Pants. But since I'm not... [shrugs]
- Brandon: So what's with your new look? It's very whore couture.
- Olive: Oh, haven't you heard? I'm the new school slut.
- Brandon: You know, I did hear something. I also heard he was twice your age.
- Olive: Oh, no no no no. He was a freshman in college.
- Brandon: I also heard he gave you crabs.
- Olive: Ew! People suck!
- Brandon: Tell me about it.
- Todd: [referring to the student protesters] Screw all these people, Olive!
- Olive: Haven't you heard? I already did.
- Rosemary: I had a similar situation when I was your age. I had a horrible reputation.
- Olive: Why?
- Rosemary: Because I was a slut. I slept with a whole bunch of people. Mostly guys.
- Olive: Mom!
- Olive: Does it ever bother you that your boyfriend is 22 years old and still in high school?
- Marianne: Because, Olive, it's His choice!
- Olive: Oh, really? His choice? He just wants to be repeating his senior year for, like, the fourth time 'cause he can't pass a single test?
- Marianne: No, silly, [gestures up] His. His, with a capital H. If the Good Lord had wanted Micah to graduate, he would have given him the right answers.
- Olive: [laughs] I'm sorry, but, I mean, really? You gotta be shittin' me, woman.
- Brandon: I'm looking for an Olive.
- Rosemary: There's a whole jar of them in the fridge.
- Brandon: I thought this was...
- Rosemary: Oh come on in. Any friend of Olive's is a friend of our daughters.
- Rhiannan: I liked Todd much better when he was topless.
- Olive: Even dressed as a woodchuck I still fantasize about him.
- Mr Griffith: I don't know what your generation's fascination is with documenting your every thought...but I can assure you, they're not all diamonds. "Roman is having an OK day, and bought a Coke Zero at the gas station. Raise the roof." Who gives a rat's ass?
- Olive: He got a Coke Zero again? Oh that Roman, incorrigible.
- Let's not and say we did.
- The rumor-filled totally FALSE account of how I ruined my flawless reputation.
- Emma Stone – Olive Penderghast
- Penn Badgley - Woodchuck Todd
- Amanda Bynes - Marianne Bryant
- Dan Byrd - Brandon
- Thomas Haden Church – Mr. Griffith
- Patricia Clarkson – Rosemary Penderghast
- Stanley Tucci - Dill Penderghast
- Cam Gigandet - Micah
- Lisa Kudrow – Mrs. Griffith
- Malcolm McDowell - Principal Gibbons
- Alyson Michalka - Rhiannon "Rhi" Abernathy
- Fred Armisen - Pastor Bryant