chunk: In an upscale New York City mansion, wealthy and popular teenager Kathryn Merteuil (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 sheltered and na誰ve Cecile. Kathryn's step-brother Sebastian (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, who had dumped her for Cecile. Kathryn asks Sebastian to seduce Cecile; he refuses as he is planning to seduce Annette Hargrove (Witherspoon), the virgin daughter of their school's new headmaster. Annette is a 'paradigm of chastity and virtue' who recently wrote a published essay about saving herself for marriage and has been temporarily staying with Sebastian's aunt. The two make a wager: if Sebastian fails to bed Annette, Kathryn gets Sebastian's