Cruel Intentions

The plot concerns a wager made between two wealthy, unscrupulous Manhattan step-siblings: Kathryn Merteuil and Sebastian Valmont. Sebastian, who has a strong reputation of deflowering young debutantes, is challenged by Kathryn to seduce Annette Hargrove, a virgin recently moved to Long Island from Kansas City, Kansas. Annette's father is the headmaster of the private school that the three attend, and Annette is coincidentally staying with Sebastian's aunt while her father relocates. If Sebastian wins, he gets one night of unbridled passion with Kathryn — something she has constantly refused him in the past — but if he fails, Kathryn receives Sebastian's prized car, a 1956 Jaguar XK140 Roadster.

Upon first meeting each other, Annette is repulsed by Sebastian, claiming she is waiting for true love before losing her virginity. She also says that she has been well-informed of his dubious reputation, but refuses to reveal who has badmouthed him. After visiting his openly gay friend Blaine Tuttle, Sebastian discovers that popular all-star football player Greg McConnell is also from Kansas City and is friends with Annette. This leads Sebastian to believe that Greg is probably Annette's secret informer. Sebastian also learns that Greg is a closeted bisexual secretly involved with Blaine. Sebastian succeeds in blackmailing Greg by taking photos of him in bed with Blaine, but learns that Greg was not actually the informer. Sebastian then makes a bribe: in exchange for keeping quiet about Greg's bisexuality, Greg must promise to talk with Annette and convince her that Sebastian's negative reputation is entirely false. Greg keeps his promise and Annette begins to reconsider, believing that Sebastian may truly be a nice person with good intentions.

In the meantime, Kathryn concerns herself with Cecile Caldwell, a young, naïve freshman who looks up to Kathryn, the student body president of their prep school. Cecile's mother, Bunny Caldwell, entrusts Kathryn with the duty of watching over her young, inexperienced daughter. However, instead of acting as a role model, Kathryn plots revenge, because her ex-boyfriend Court Reynolds recently dumped her in favor of Cecile. Cecile is not aware of Kathryn's previous relationship with Reynolds; she seems more interested in her music instructor, an African-American cellist and composer named Ronald. Kathryn begins subtly corrupting Cecile in various ways, such as telling her to sleep with as many men as possible in order to satisfy Ronald and showing her how to kiss. Kathryn instructs Sebastian to seduce and deflower Cecile, which he gladly does after discovering that Annette's informant is none other than Cecile's mother, Bunny, whom he already disliked. Kathryn then double-crosses Cecile and tells Bunny Caldwell about her daughter's affair with Ronald. Bunny Caldwell abruptly confronts and fires Ronald over the affair. Kathryn herself has a brief tryst with Ronald; however, he and Cecile secretly remain in a relationship.

After working his way into Annette's heart, Sebastian finally tells her that true love is right in front of her and, in keeping with her earlier claim to be "waiting for true love," she will be a hypocrite if she turns her back on him now. Confused and distraught, Annette believes she and Sebastian really are in love and then finally relinquishes herself to him. Just as he's about to win his bet with Kathryn by taking Annette's virginity, however, Sebastian himself is then overcome with guilt and confusion, and he abruptly leaves without explanation. Sebastian realizes that he actually has fallen in love with Annette, and the wager is now of little importance to him.

The following morning, Kathryn wakes Sebastian and informs him that whatever he said or did to Annette the night before has caused Annette to flee from his aunt's house. Moved by his newfound love, Sebastian embarks on a citywide search for her. After a tip-off from Greg, Sebastian tracks Annette down at a train station, where they embrace. The two lovers then consummate their feelings in Sebastian's bed, winning him the bet at last.

A few days later Kathryn overhears Sebastian professing his love to Annette over the phone. She proceeds to mock him, claiming that falling in love with his "target" has stripped him of his masculinity and macho reputation. Sebastian, taken aback, then claims otherwise, stating that the bet still stands and that he has no real feelings for Annette. To prove this, he goes to Annette and lies to her, telling her she was "just a conquest" and that their relationship means nothing. Annette breaks down crying and angrily throws him out of her house.

Sebastian then goes to Kathryn and tells her that he has broken up with Annette for her. He demands she now uphold her end of their wager. Kathryn cruelly informs Sebastian that the entire bet was just a means of manipulating him into a vulnerable state for her amusement; she mocks him for having abandoned the only girl he ever really loved just to uphold his sleazy reputation, and tells him that she has no intention of upholding her end of the bargain. Devastated by this betrayal, Sebastian storms out, desperate to win back Annette.

When Sebastian goes to Annette she refuses to see him, so he leaves her his journal, which discloses the truth about his life and myriad personal secrets he had been hiding from her: Kathryn's true evil nature, the bet they had made together, and the entirety of his sordid reputation.

Meanwhile, a vengeful Kathryn calls Ronald and manipulates him, saying that Sebastian hit her in a rage (seen on the DVD in a deleted scene), and further revealing that Sebastian had recently had sex with Cecile. Infuriated by this news, Ronald goes searching for Sebastian. As Sebastian is walking to meet Annette, he is confronted by an angry Ronald and the two begin to brawl in the street. Annette sees this and hurriedly goes to help Sebastian, but Ronald accidentally knocks her right into traffic. Right as she is about to be hit by a taxi, Sebastian heroically pushes her out of the way and is hit by the taxi instead. His last words to her are "I love you, Annette," before he dies.

The film then skips forward in time to the beginning of the new school year that autumn, where Sebastian's memorial service is taking place at the prep school chapel. Kathryn is shown getting ready for a eulogy while snorting cocaine in the bathroom from a crucifix. Annette enters — the first and only time the two girls actually meet face to face — and offers her sympathy, which Kathryn arrogantly shrugs off. Before leaving, Annette tells her, "Sometimes when I feel I can't go on, I turn to Jesus and he helps me through it," a phrase that Kathryn had often insincerely offered to numerous others during the earlier portions of the film. It is also a twist on the cross she wears, it being filled with cocaine. She relishes flirting with danger by waving her habit under their noses.

Kathryn leaves to deliver her eulogy. During her speech she lies about her high morals and her compassion for her stepbrother, but halfway through her eulogy she is interrupted by several people walking in and handing out booklets in the back, causing people to begin leaving the service. Unnerved, Kathryn angrily storms outside to see what's going on. When she steps outside, she is greeted by the sight of crowds of students and faculty reading photocopies of Sebastian's journal, appropriately titled "Cruel Intentions." It is then revealed that Sebastian's journal has been copied and handed out to every person attending the funeral, destroying Kathryn's reputation and finally exposing her true colors to the entire community. She is handed a copy by Cecile, and starts crying upon reading its contents, including the full plot against Annette, and finally seeing Sebastian's true (negative) feelings for his stepsister. The headmaster approaches Kathryn and pulls apart her crucifix, revealing the cocaine hidden inside and furthering Kathryn's ruin.

The last scene, featuring The Verve's "Bitter Sweet Symphony", shows Annette driving away in Sebastian's Jaguar with the original journal on the passenger seat (mirroring one of the opening shots) and putting on Sebastian's sunglasses, ending the film on a bittersweet note and suggesting that it was she who distributed the photocopies. The camera pans out, New York City's skyline is then seen.