Sabastin (Ryan Philip Ryan Phillippe) and Catherine (Sarah Michelle Gella Sarah Michelle Gellar) were originally the children of two families because of the union of their parents to become two siblings. The two started a game out of selfishness. if Sabastine loses, his luxury sports car will be owned by Catherine; if he wins, Catherine will provide him with overnight service. The game is that Sabastin has to get the principal's daughter Annie (Reese Witherspoon Reese Witherspoon). Although he has fucked countless girls in Manhattan, it has been difficult for Anne, who once wrote in 17 magazine that she would keep her virginity for her wedding night. Sabastin certainly did his best for this difficult sex hunt, but to his surprise, the game became more and more complex than he had expected.