Plot
The wealthy and popular Kathryn Merteuil (Gellar) takes the sheltered and naïve Cecile Caldwell (Blair) under her wing, promising to turn Cecile into a model student. Kathryn's real intention, however, is to use Cecile to indirectly take revenge on Court Reynolds, her ex-lover, who had dumped her for Cecile. Kathryn asks her step-brother, Sebastian Valmont (Phillippe) to seduce Cecile; he refuses as he is planning to seduce virgin Annette Hargrove (Witherspoon) - a 'paradigm of chastity and virtue' and spoil her social reputation. Doubting Sebastian's chance of success, they make a wager: If Kathryn wins, she gets Sebastian's vintage 1956 Jaguar XK140 roadster; if Sebastian wins, Kathryn will allow him to "put it anywhere" (an oblique reference to anal sex). Sebastian agrees.
Ronald Clifford, Cecile's music teacher, is also in love with Cecile. Annette is temporarily staying with Helen Rosemond, Sebastian's Aunt. Cecile's mother, Mrs. Caldwell, who met Annette at her school, has already warned Annette of Sebastian's reputation for womanizing. Sebastian's seduction of Annette fails. Wanting revenge on the Caldwells, Sebastian tells Kathryn he will now seduce Cecile. Kathryn tells Cecile's mother about Ronald and Cecile's romance and Mrs. Caldwell intervenes in her daughter's relationship. Sebastian, in turn, calls Cecile to his house, ostensibly to give her a letter from Ronald. Sebastian 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.
Sebastian falls in love with Annette, who returns his feelings but resists him. Sebastian calls her a hypocrite because she claims to be waiting for her one true love, but when her one true love chooses to love her back, she resists. She relents, but Sebastian, in turn, refuses her. Annette flees to her friend's parents' estate. Sebastian tracks her down and professes his love, and they make love. As he has won the bet, Kathryn offers herself to Sebastian the next day, but he refuses; he now wants Annette only. Kathryn taunts him and threatens to ruin Annette's reputation, so Sebastian pretends indifference to Annette and coldly breaks up with her.
After Sebastian tells Kathryn that he has broken up with Annette and arranged for Cecile and Ronald to be together, Kathryn reveals that she has known all along that he was truly in love with Annette and manipulated him into giving her up. She then rejects him. Sebastian leaves, and Kathryn calls Ronald to inform him that Sebastian had sex with Cecile. Sebastian finds and sends Annette his journal, in which he has detailed all of Kathryn's maneuvers and written his true feelings for Annette. When Sebastian starts heading home, Ronald confronts him in the middle of the street and a fight ensues. Annette runs out 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. Before he dies, Sebastian and Annette profess their love for each other.
At Sebastian's funeral, Cecile distributes copies of Sebastian's journal, made into a book by Annette, titled "Cruel Intentions". Kathryn is humiliated and rejected by her former friends, and she is defamed for the cocaine hidden in her cross necklace. Annette drives away in Sebastian's Jaguar with his journal at her side as fond memories of Sebastian play through her head.
Read more about this topic: Cruel Intentions
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