Two wealthy step-siblings of an elite Manhattan prep school make a wager: to de-flower the new headmaster's daughter before the start of term.

Sebastian: You amaze me.
Kathryn: Eat me, Sebastian! It's okay for guys like you and Court to fuck everyone. But when I do it, I get dumped for innocent little twits like Cecile. God forbid, I exude confidence and enjoy sex. Do you think I relish the fact that I have to act like Mary Sunshine 24/7 so I can be considered a lady? I'm the Marcia fucking Brady of the Upper East Side, and sometimes I want to kill myself. So there's your psychoanalysis, Dr. Freud. Now tell me, are you in... or are you out?
Sebastian: I read your manifesto.
Annette: You did?
Sebastian: Yes. I must say, I found it rather... appalling.
Annette: That's a first. Most people praise me for it.
Sebastian: Most people are sheep. Who are you to criticize something you've never experienced?
Annette: I wasn't criticizing. I just think people shouldn't experience the act of love until they are in love and I just don't think people our age are mature enough to experience those kinds of emotions.
Sebastian: Are you a lesbian?
Annette: No...
Sebastian: I didn't mean to offend you. I just picked up on a little bit of that lesbian vibe.
Sebastian: What shall we toast to?
Kathryn: To my triumph.
Sebastian: It's not my choice of toast, but it's your call. To your triumph over Annette.
[Kathryn laughs]
Sebastian: What's so funny?
Kathryn: Silly rabbit. My triumph isn't over her. It's over you.
Sebastian: Come again?
Kathryn: You were very much in love with her. And you're still in love with her. But it amused me to make you ashamed of it. You gave up on the first person you ever loved because I threatened your reputation. Don't you get it? You're just a toy, Sebastian. A little toy I like to play with. And now you've completely blown it with her. I think it's the saddest thing I've ever heard.
[drinks champagne]
Kathryn: Tastes good. So, I assume you've come here to make arrangements. But unfortunately, I don't fuck losers.
Annette: I'm impressed.
Sebastian: Well, I'm in love.
[on Greg being gay]
Blaine Tuttle: He used to sneak into my dorm room drunk every night. We'd go at it for a little while, and then, as soon as he'd come, he'd start freaking out. "What are you doing, man? I'm not a fag. If you tell anybody, I'm gonna kick your ass!" God. The only reason I let him keep up the charade is because the man's got a mouth like a HOOVER, Ooooof!
Kathryn: My advice is to sleep with as many people as possible.
Cecile Caldwell: But that would make me a slut, wouldn't it?
Kathryn: Cecile, everybody does it; it's just that nobody talks about it.
Cecile Caldwell: So, it's like a secret society?
Kathryn: That's one way looking at it.
[under her breath]
Kathryn: Fucking idiot...
Kathryn: The parental units called while you were out.
Sebastian: How IS your gold-digging, whore of a mother enjoying Bali?
Kathryn: She suspects your impotent, alcoholic father is diddling the maid.
Sebastian: Good.
Cecile Caldwell: This sure doesn't taste like an iced tea.
Sebastian: It's from Long Island.
Sebastian: We've done some pretty fucked up shit in our time but this... I mean, we're destroying an innocent girl. You do realize that?
Mrs. Sugarman: Oh, did I ever tell you the time, when my late husband sent me...
Sebastian: Yes, you already did, Mrs. Sugarman.
Mrs. Sugarman: Oh, I did?
Sebastian: Right after we played backgammon, Mrs. Sugarman.
Mrs. Sugarman: Oh! We played backgammon?
Sebastian: Uh huh. You beat me three times.
Mrs. Sugarman: I did?
Sebastian: Yup. Then I fucked your daughter.
Mrs. Sugarman: Excuse me?
Sebastian: I said, would you care for some water?
Mrs. Sugarman: No, thank you.
Sebastian: You spend all your time preaching about waiting for love. Well here it is. Right in front of you, and you're going to turn your back on it. So I guess we're just fucked. I'll move on. But you are going to have to live the rest of your life knowing that you've turned your back on love. And that makes you a hypocrite. Have a nice life.
Bunny Caldwell: How do you do it? Where do you get your strength?
Kathryn: [pulling out her cross that doubles as a cocaine dispenser] Well I know this sounds corny, but whenever I feel the temptation of peer pressure, I turn to God and he helps me through the problem.
Bunny Caldwell: Oh, that's beautiful.
Bunny Caldwell: How dare you treat me with such disrespect! I got you off the streets and this is how you repay me?
Ronald Clifford: Got me off the streets? I live on 59th and Park!
Bunny Caldwell: Whatever!
[Cecile is wearing a shirt with a big koala bear on it]
Sebastian: My, what an adorable shirt you're wearing!
Cecile Caldwell: Thanks, my dad took me on a trip to Australia.
Sebastian: And how are things down under?
[looks up her skirt]
Sebastian: Blossoming, I hope.
Marci Greenbaum: [into a phone; crying] He told me loved me, and I believed him.
Dr. Greenbaum: [into a phone] Alright, just calm down. Take a deep breath, step out of the circle...
Marci Greenbaum: Would you cut your psycho-babble bullshit, Mom! There's pictures of me on the internet!
Dr. Greenbaum: What kind of pictures?
Marci Greenbaum: Nude pictures, what do you think?
Dr. Greenbaum: JESUS CHRIST! How could you be so stupid?
Marci Greenbaum: He was just so charming, and kept saying how I had killer legs, and how he wanted to photograph them, and things just got completely out of hand.
Sebastian: [voice-over] Dear Annette, I don't know what I could possibly say that would rectify the harm I've caused you. The truth of the matter is that being with you was the only time I have ever been happy. My whole life has been a joke. I prided myself on taking joy in others' misery. Well, it finally backfired. I succeed in hurting the first person I ever loved. Enclosed is my most prized possession. My journal. For a long time I considered it my trophy. A sordid collection of my conquests. If you really want to know the truth than please read it. No more lies. Please give me another chance. I'm a wreck without you.
Sebastian: I have a reputation to uphold.
Kathryn: Oh, but diddling the therapist's daughter is a challenge.
Sebastian: [grinning] She was overcharging.
Kathryn: [into a phone] Fuck her yet?
Sebastian: [into a phone] I'm working on it.
Kathryn: Loser!
Sebastian: Blow me!
Kathryn: Call me later?
Sebastian: Sure.
[hangs up]
Sebastian: E-mail is for geeks and pedophiles.
Kathryn: Oh, Sebastian? That little wager of yours? Count me in.
Sebastian: What are the terms?
Kathryn: If I win, then that hot little car of yours is mine.
Sebastian: And if I win?
Kathryn: [Takes off her jacket to reveal a skimpy-looking tank top] I'll give you something you've been obsessing about ever since our parents got married.
Sebastian: Be more specific.
Kathryn: In English? I'll fuck your brains out.
Sebastian: [a little shocked for a moment, recovers] What makes you think I'll go for that bet? That is a 1956 Jaguar Roadster.
Kathryn: Because I'm the only person you can't have, and it kills you.
Sebastian: No way.
[Starts to exit the room]
Kathryn: You can put it anywhere...
Sebastian: [Stops in his tracks, bites his lip] You've got yourself a bet, baby.
[they shake hands and Sebastian exits]
Kathryn: Happy hunting, Sebastian.
Kathryn: I hate it when things don't go my way. It makes me so horny.
Sebastian: She has a boyfriend named Trevor. Been going out for a year... Trevor understands.
Kathryn: Trevor's a fag.
Bunny Caldwell: Keep your legs together. This isn't Jamaica.
Sebastian: Why can't we be together?
Annette: You wanna know why? Because I don't trust myself with you.
Kathryn: She's quite cute, you know? Young, supple breasts, a tight, firm ass... uncharted pooty... Be her Captain Picard, Valmont. Boldly go where no man has gone before.
Sebastian: You could be a model. It's too bad you're not sexy.
Kathryn: Unfortunately, our Don Juan is moving with the speed of a Special Olympics hurdler.
Kathryn: Can I take my new car for a ride?
Sebastian: Kathryn, the only thing you'll be riding is me.
Kathryn: I think there's something going on between Cecile and her music teacher.
Bunny Caldwell: Ronald? That's crazy.
Kathryn: I know. She's so young, and he's so...
Bunny Caldwell: Black!
[Store Clerk sets down a cup of coffee]
Bunny Caldwell: Brown sugar. No sugar.
Ronald Clifford: The black man is Gone! The Black man is gone!
[Cecile returns home in the morning with her clothes rumpled and hair disheveled]
Bunny Caldwell: Jesus Christ, where have you been?
Cecile Caldwell: Shopping.
Annette: I don't know if this'll help. But sometimes when I'm feeling down, I turn to Jesus and he helps me through it.
Kathryn: Thank you.
Annette: All right, well, I'll see you around campus.
Kathryn: Looking forward to it... Freak.
Sebastian: I can't believe that there was a time in my life when all I could think about was... sex
Dr. Greenbaum: That's no way to go through life.
Kathryn: [takes her hand off his crotch] Down, boy.
Ronald Clifford: I would like to think that in these times someone of your stature could look beyond racial lines.
Bunny Caldwell: Oh, don't give me any of that racist crap! My Husband and I gave money to Colin Powell!
Ronald Clifford: I guess that puts me in my place.
Kathryn: Everybody loves me, and I intend to keep it that way.
Sebastian: Well... it's too bad that Greg's in Kansas this summer.
Blaine Tuttle: Not any more. Football practice just started last week. He's back in the dorms.
Sebastian: Do you think you can arrange a little pillow-kissing session with him?
Blaine Tuttle: I do belive that Sparticus is playing on TV tonight.
Kathryn: I wanna FUCK!
Sebastian: And I don't.
Annette: [on the phone] What are you reading?
Sebastian: A Tale of Two Cities.
Annette: Oh, I love Dickins.
Sebastian: Me too. Hang on its the other line.
[turns to the two hookers on his bed. One is in a thong the other has her hand on the first one's butt]
Sebastian: Keep stroking.
[talk to Annette]
Sebastian: Sorry, that was my mom.
Kathryn: Introduce her to your world of sex, drugs and... what else do you do?
Sebastian: Read this.
[puts down a copy of "seventeen" magazine on the table]
Kathryn: I know how to alleviate menstrual cramps, thank you very much.
Sebastian: It's not like you have a husband - unless you're married to Jesus.
Sebastian: Ohh well, duty calls. Dr. Greenbaum and her daughter should make for interesting entry.
Kathryn: Ohh, your journal. Could you be more queer?
Sebastian: Could you be more desperate to read it?
Cecile Caldwell: He took down my pants and he started writing the alphabet but he was writing it with his tongue.
Sebastian: Sounds great... I love you too.
Kathryn: [mocking Sebastian] "I love you"? My God. You are completely pussy-whipped.
Sebastian: Stop it.
Kathryn: What happened to us?
Sebastian: Nothing's changed.
Kathryn: Yes it has. You're in love with her, you don't love me anymore.
Sebastian: Come on, Kathryn, it's just a bet.
Sebastian: [after being kissed by Kathryn and pushing her away] This is ridiculous.
Kathryn: What's ridiculous, dear brother, is you! Look at yourself, look at what you've been reduced to! Have you given any thought to what's going to happen when school starts? Not only are you dating Miss Seventeen Magazine, but she's also the new headmaster's daughter. Before you know it, you'll be giving campus tours with her. Oh, wait, her father doesn't know about your past, does he? I doubt he'd let his little princess be seen with the likes of you. Hmm... It's so disappointing to see Annette's manifesto was a total sham. Though, as student body president, I feel it's my sworn duty to tell him.
[picks up the phone and starts dialing]
Sebastian: Put the phone down.
Kathryn: Shh, this will only take a second.
Kathryn: [after Sebastian grabs the phone and slams it down] Hmm, quite the predicament you're in.
Sebastian: I don't care what you say. The fact of the matter is that I was planning on telling her everything this afternoon.
Kathryn: Oh, that's right, I forgot, you're so in love. Do you honestly believe you've done a complete 180 in the few days you've known her? Well let me tell you something, people don't change overnight. You and I are two of a kind. At least I have the guts to admit it. You were going to leave school a legend, now you're going to leave a joke.
Sebastian: Well, I'm willing to take my chances.
Kathryn: Don't do it, Sebastian. Not only will you ruin your reputation, you'll destroy hers.
Kathryn: [on the phone] Cecile?... OK, stop crying... stop crying... You know... hold on for Sebastian.
Sebastian: Cecile?... Stop crying.
Greg McConnell: So I pull out my dick, and I shove it right in her face. And I'm like, the hell is this? Grandma with a birthday present? Suck it ya dumb bitch!
[reading a virgin's manifesto]
Kathryn: "Why I Plan to Wait" by Annette Hargrove, Kansas City, Kansas. Jesus Christ, is she for real?
Sebastian: Oh, she's daddy's little angel, a paradigm of chastity and virtue.
Helen Rosemont: Sebaaaastian!
Sebastian: [Under his breath] Aw fuck me.
[Hugging Helen]
Sebastian: Aunt Helen! God I've missed you!
Blaine Tuttle: Now, just think for a minute. This girl... Annette Hargrove, she said someone wrote her a letter explaining all about you. Where did you say she was from?
Sebastian: Kansas. Who the hell do I know in Kansas?
Blaine Tuttle: Greg McConnell.
Sebastian: The football stud?
Blaine Tuttle: Mm hm. He's from Kansas City. I wouldn't be surprised if he was your rat.
Sebastian: It would make sense... McConnell hates me. I fingered his girlfriend at Homecoming last year.
Blaine Tuttle: I... don't think that bothered him so much.
Sebastian: What do you mean?
Blaine Tuttle: Well, let's just say that Greg likes to tackle the tight ends both on AND off the field.
Sebastian: Oh, are you shitting me?
Blaine Tuttle: I shit you not. He used to sneak into my dorm room, drunk, every month. We'd go at it for a little while, and then as soon as he'd come, he'd start freaking out: "Oh, what are you doing, man? I'm not a fag! If you tell anybody I'm gonna kick your ass!" Gah. The only reason I let him keep up this charade is cause the man's got a mouth like a Hoover. Ooof!
Kathryn: [referring to Annette] She's really getting to you, isn't she?
Sebastian: If you must know, yes. I can't stand that holier-than-thou bullshit, and yet, I'm completely infatuated with her.
Sebastian: She made me laugh.
Cecile Caldwell: [Kathryn is watching Cecile from a video cam] Peace out.
Kathryn: Peace out? What a moron.
Annette: People shouldn't experience the act of love until they are in love.
Kathryn: Keep your friends close, and your enemies closer. When I'm through with Cecile, she'll be the premiere tramp of the New York area.
Annette: I don't believe you.
Sebastian: There's something I have to tell you.
Annette: Tell me.
Sebastian: This isn't working out for me anymore.
Annette: [not taking Sebastian seriously] Yeah, me neither.
[kisses Sebastian and he doesn't respond]
Annette: What's wrong?
Sebastian: It's not you. It's me... I'm completely fucked up.
Annette: What are you saying?
Sebastian: I thought I was in love with you but it was just a lie.I wanted it to work but unfortunately, I feel nothing.
Annette: Why are you doing this?
Sebastian: I just... I just wanted to see what you were like in bed.
Annette: You don't mean that.
Sebastian: You know nothing. You don't even know me!The fact of the matter is, there is someone I love. You don't even compare to her.
Sebastian: I don't know how to make this any clearer to you. You mean nothing to me!You were just... You were just a conquest.
Annette: You're such a coward.Look at yourself! You're shaking! Is that what you came to tell me?
Sebastian: I'm sorry. I'm completely...
Annette: Yeah, you're completely fucked up!Get out!
Annette: Get out!
Annette: [Sebastian tries to touch Annette] Don't touch me! Don't touch me!
[Tries to touch her again]
Annette: Don't fucking touch me Sebastian!
[Slaps Sebastian around the face]
Annette: Just leave
[after Sebastian leaves Annette starts crying]
Sebastian: I didn't know it was asshole day at the Valmont house.
Kathryn: Who are you spying on? That her?
Sebastian: Yeah
Kathryn: Aww, she's crying. Little baby upset about the big bad book.
Sebastian: Shut up!
Kathryn: What's up your ass?
Sebastian: I can't win with you.
Annette: It's not all about winning, Sebastian.
Annette: How can someone so charming be so manipulative?
Sebastian: Get your ass on the bed and prepare for the fuck of your life. After what you put me through I deserve it.
Kathryn: [after kissing] See? That wasn't so scary.
Cecile Caldwell: It was nothing.
Kathryn: Okay, let's try it again only this time I'm gonna stick my tongue in your mouth, and when I do that I want you to massage my tongue with yours. And that's what first base is.
Cecile Caldwell: Okay!
Kathryn: Eyes closed.
[they french kiss]
Kathryn: Not bad.
Cecile Caldwell: That was cool!
Gretchen (a hooker): Books are for fags.
Sebastian: Books are for fags? Then weep for the future.
Annette: [Reciting lines from the letter written to her warning her to stay away from Sebastian] Even more treacherous than he is attractive, he has never uttered a single word without some dishonorable intention. Every woman he has successfully pursued has regretted it. Stay away from him.
Sebastian: Unbelievable! Some fag, no offense...
Blaine: None taken.
Sebastian: Wrote a letter to this chick describing my lascivious tactics.
Blaine: Any ideas who it could be?
Sebastian: Blaine, if I knew who it was, that person would be in a momentous amount of pain!
Kathryn: You're telling me you had the chance to fuck her and you didn't? God, are you a chump.
Sebastian: A momentary lapse of judgment, soon to be rectified.
Annette: You know what your problem is? You take yourself way too seriously.
Sebastian: I do not.
Annette: You should lighten up.
Sebastian: I am lightened, can we drop this?
Annette: Okay.
[Makes a face at Sebastian]
Sebastian: Will you stop that?
Annette: [Continues to make a face]
Sebastian: Stop, it's distracting
[starts to laugh]
Annette: Are you laughing?
Sebastian: [seriously] No.
Annette: No?
[Makes another face, Sebastian begins to laugh and then regains control]
Annette: Its okay you can laugh, I promise I won't tell anyone.
[Sebastian has just caught Greg in bed with Blaine]
Greg McConnell: This could ruin my career, man...
Sebastian: Your career? Greg, think about your family. Can you imagine the pain and humiliation your father is going to feel when he finds out that his pride and joy is a fudge-packer?
Greg McConnell: Valmont, please! Let's just forget about this...
Sebastian: [Pretends to ponder for a beat] No. Sorry, can't help you there. After all, it is you who's been bad-mouthing me to Annette Hargrove.
Greg McConnell: [Panicking] Annette Hargrove? I don't know what you're talking about!
Sebastian: You're the only one who knows her. The truth will save you.
Greg McConnell: I never said a word to her about you. I promise!
Sebastian: Yeah, right.
Blaine: Come to think of it, Valmont, he is probably telling you the truth. The man can barely write out a shopping list, let alone a letter. What was I thinking!
Kathryn: [mocking Sebastian] "I love you"? My God. You are completely pussy-whipped.
Greg McConnell: [Sebastian walks in on Blaine and Greg fooling around] Shit! Give me my fucking underwear!
Blaine Tuttle: All right! Don't get so huffy!
Sebastian: She made me laugh.
Sebastian: Cecile, you know what would be super-duper sexy? If you lost all the clothes.
Cecile Caldwell: I don't think so.
Annette: I don't know. Relationships seem too distracting. I'd rather concentrate on my studies.
Helen Rosemont: Sebastian, I want you to meet Annette.
Sebastian: Well, well.
Annette: Hello.
Helen Rosemont: She'll be staying with me for a while.
Sebastian: I guess that makes two of us. Aunt Helen, why don't you go inside and whip us up some of that iced tea of yours. I'll... tend to Annette.
Helen Rosemont: All right. You two don't get into any trouble.
Annette, Sebastian: We won't.
Sebastian: Night Sweetpea.
Annette: I wouldn't expect a man of your experience to understand my beliefs.
Sebastian: [taken off-guard] Uh... what's THAT supposed to mean?
Annette: I've been very well-informed of your reputation.
Sebastian: What have you heard?
Annette: That you promise girls the world in order to get them in bed with you.
Sebastian: [after a pause; more stunned] Who told you this?
Annette: A friend wrote me.
Sebastian: That's a little tacky.
Annette: Why do you sound so surprised? It's the truth isn't it?
Sebastian: [walks away; shrugs] If you say so.
Sebastian: I'm sick of sleeping with these insipid Manhattan debutantes. Nothing shocks them anymore.
Cecile Caldwell: [Cecile is playing the cello badly] I suck! I SUCK!
Bunny Caldwell: How do you do it? Where do you get your strength?
Kathryn: [Pulling out her cross that she hides her coke in] I know this will sound corny, but, whenever I feel the temptation of peer pressure, I turn to God and he helps me through the problem.

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