Cruel Intentions

“In the game of seduction, there is only one rule: Never fall in love.”

Summer on Manhattan's Upper East Side, and the rich teenagers at one elite prep school have nothing to do but watch each other. Kathryn Merteuil (Sarah Michelle Gellar) bets her stepbrother Sébastian Valmont (Ryan Phillippe) that he can't seduce Annette Hargrove (Reese Witherspoon), the headmaster's daughter, before the season ends. Roger Kumble sets the wager between the two stepsiblings, who share a house, a taste for games, and very little affection.