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Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe) are two rich, spoiled teenagers from the most luxurious part of Manhattan. They are also step-siblings, as their disgustingly wealthy parents have married each other. The term "golden youth" does not even come close to describing their decadent lifestyle. Sebastian has met all the beautiful girls in Manhattan, and Kathryn is also incredibly promiscuous for her age. This makes her all the more furious when she gets dumped by her boyfriend, who has traded her refined charm for the virginal innocence of naive Cecile (Selma Blair). Kathryn therefore makes a devilish and appropriately vengeful bet with her little brother. If playboy Sebastian, whom no girl has ever been able to resist, takes Cecile's virginity and also manages to seduce another angelic innocent, Annette (Reese Witherspoon), his stepsister will give him a night of unearthly pleasure. If Sebastian loses, he will lose his beloved 1956 Jaguar...

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