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Kathryn Merteuil (Sarah Michelle Gellar), the image of social perfection, takes the sheltered and naive Cecile Caldwell (Selma Blair) under her wing, promising to turn Cecile into a model student like herself. Kathryn's real intention, however, is to take revenge on her ex-lover, who had dumped her for the "innocent little twit" Cecile. She intends to corrupt Cecile by getting her to sleep with as many men as possible, thereby destroying her reputation and teaching her ex-lover a lesson.

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She asks for the help of her womanizing step-brother, Sebastian Valmont (Ryan Phillippe). Though Kathryn and Sebastian have collaborated in schemes of manipulation before, he initially refuses. He is busy planning another "conquest" Annette Hargrove (Reese Witherspoon), the woman who has written a manifesto saying she plans to keep her virginity intact and wait for marriage. Fortunately for Sebastian, she is temporarily staying at his aunt's estate. Kathryn does not think he has a chance with Annette, so they make a wager. If Kathryn wins, she gets Sebastian's vintage Jaguar, a 1956 XK140 Roadster, if she loses, Sebastian gets to sleep with Kathryn something she has been denying him ever since their parents married.

Meanwhile, Kathryn teaches Cecile what "first base" is by making out with her. She then encourages her to try it out with her music teacher, Ronald (Sean Patrick Thomas), who is also smitten with Cecile. Kathryn makes arrangements for Ronald and Cecile to spend time together, hoping that he will take Cecile's virginity.

Sebastian, on the other hand, has a hard time seducing Annette. Though they have chemistry, she sees right through him and rejects his advances. He learns that Annette has been forewarned of his libertine ways by none other than Cecile's mother. Wanting revenge, he joins Kathryn in her plans to corrupt Cecile.

Kathryn engineers Ronald's break-up with Cecile by informing Cecile's mother. Sebastian, in turn, calls Cecile to his house to give her a letter from Ronald. Once at his house, he blackmails Cecile and performs oral sex on her. The next day, Cecile confides in Kathryn, who advises her to learn the art of sex from Sebastian so that she can make Ronald happy in bed.

Meanwhile, Sebastian begins to genuinely fall in love with Annette, who returns his feelings but still keeps her defenses up. He accuses her of being a hypocrite she preaches to wait for love, and yet refuses to sleep with the guy she loves. Annette relents, but Sebastian, now feeling guilty, refuses. However, when she leaves the estate, heartbroken, he tracks her down and they consummate their relationship.

The next day, Kathryn offers herself to Sebastian as part of the bet but he refuses. She taunts him for having gone soft, then convinces him that his love for Annette is nothing more than a passing infatuation. Finally swayed by Kathryn's threat to ruin Annette's reputation, Sebastian breaks up with Annette and returns to Kathryn, who now refuses to sleep with him. After Sebastian tells Kathryn that he has arranged for Cecile and Ronald to be together, she reveals that she has known all along that he was truly in love with Annette, yet she manipulated him to give it up. While Sebastian may have initially won the bet, she made him lose his first true love, and she, Kathryn, does not sleep with "losers."

Sebastian realizes his mistake. He sends Annette his journal, in which he has detailed all his previous "conquests", but written his true feelings for Annette, hoping she would learn the truth for herself and forgive him. Kathryn meanwhile, informs Ronald of Sebastian's affair with Cecile whilst informing that Sebastian had hit her, making Ronald very angry. Ronald confronts Sebastian in the middle of the street and a fight ensues. Annette, in search of Sebastian, comes upon the fight and tries to stop it. She is thrown into the way of an oncoming cab. Sebastian pushes her to safety and is hit by the speeding cab himself. Annette rushes to his side. Before he dies, he professes his love for her, and she reciprocates.

At his funeral, Kathryn gives a speech to the school about how she had tried to get Sebastian to mend his ways and become a model student like herself. Halfway through her speech, students start walking out. Cecile is distributing copies of Sebastian's journal to all the students. The journal shows all of Sebastian's inner thoughts: his conquests, his description of the bet, and a page on Kathryn, which finally illustrates her manipulative and deceitful ways, including the fact that she hides a vial of cocaine in a crucifix she wears round her neck. The headmaster takes Kathryn's crucifix and opens it, emptying the cocaine. Kathryn's spotless reputation is destroyed, and people finally see her for the troubled, callous mastermind that she is.

In the final shot, Annette drives away in Sebastian's Jaguar, putting his sunglasses on, with his journal by her side.