In an upscale New York City mansion, wealthy and popular teenager Kathryn Merteuil (Sarah Michelle Gellar) is discussing her prep school with Mrs. Caldwell (Christine Baranski) and Mrs. Caldwell's daughter, Cecile (Selma Blair). Kathryn promises Mrs. Caldwell that she will look out for the naive Cecile. Kathryn's stepbrother, Sebastian (Ryan Phillippe), enters the room, whereupon Mrs. Caldwell reacts to him coldly and leaves with Cecile. Kathryn reveals to him that her real intention is to use Cecile to take revenge on her ex-lover Court Reynolds (Charlie O'Connell), who dumped her for Cecile. Kathryn asks Sebastian to seduce Cecile; he refuses as he is planning to seduce Annette Hargrove (Reese Witherspoon), the virgin daughter of their prep school's new headmaster who is a "paradigm of chastity and virtue". After some negotiation the two agree on a wager: if Sebastian fails to bed Annette, Kathryn gets Sebastian's vintage Jaguar XK140; if he succeeds, Kathryn will have sex with him (and anal sex is implied as Kathryn seals the bet by promising him that "you can put it anywhere" as she gestures suggestively to him). It is mentioned that Sebastian keeps a journal detailing his conquests.