Karthryn challenges, and dares her stepbrother to seduce the newly arriving Annette. The two even agree to a small wager on the matter. If Sebastian fails to steal the innocence from this girl then he will lose his Jaguar. If he wins, Kathryn will let her stepbrother "put it anywhere." So the wager in essence is a car and the reward is anal sex with Buffy. Who could refuse?

On the day that Annette arrives, Sebastian learns that Annette has heard of Sebastian's horrible reputation. Sebastian wonders who said what and when. Sebastian blackmails a friend of Annette's into saying good things about Sebastian. A poloroid of someone engageing in homoerotic activities was all Sebastian needed to achieve this.

Sebastian proceeds with his best to wear down the defenses of Annette. It seems poor Sebastian is set to lose his battle with Annette, but the tides do turn. Sebastian calls innocent Annette a hypocryte for refusing to let herself love someone. Sebastian is then granted access to Annette but then chickens out after developing a concience of sorts. But this was only a tempoary thing. Sebastian goes back and reclaims his prize.

While this conquest has been going on, Kathryn, and Sebastian have had other schemes in place as well. Kathryn schemes to corrupt a girl into a loose lifestyle. Kathryn even teaches her how to kiss. Buffy kisses girls as easily as guys it seems, how beautiful.

In the end Sebastian breaks up with Anette the one girl he truly was starting to love. He did this because of encouragment from Kathryn. Kathryn then promptly calls her stepbrother a loser and refuses to grant her part of the wager.

Sebastian then shares with Annette the diary of his life and conquests. After being scorned by Annette for so long she starts to understand. Annette then is almost hit by a car, Sebastian saves her but dies. Kathryn was planning to use the sympathy of her brother's death to launch her own popularity to higher levels but Annette has a surprise of her own for dear Kathryn.

Cruel Intentions is a movie which compares the dominating nature of sex with the mysteries of the human heart. Even a hunter (Sebastian) can learn to love what he hunts it seems. The movie features plot twists, and a vindicative callous approach to life that is humorous while at the same time romantic and evil.