In Cruel Intentions, two wealthy teenage stepsiblings, Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), begin a wicked summer of seduction and betrayal. When Kathryn is dumped by her beau, Court Reynolds, for the innocent Cecile (Selma Blair), she challenges Sebastian to turn Cecile into damaged goods. An easy feat, Sebastian raises the stakes when he bets Kathryn he can seduce the pristine Annette Hargrove (Reese Witherspoon), the new headmaster's daughter who just wrote an article about her intentions to stay pure until she marries. The stakes: if Sebastian succeeds, Kathryn must give him a night of unbridled biblical pleasure, something he's wanted since their parents got married. If he fails, he must forfeit his priceless 1956 Jaguar to Kathryn and suffer the shame of defeat.