Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.

Sarah Michelle Gellaras Kathryn Merteuil
Ryan Phillippeas Sébastian Valmont
Reese Witherspoonas Annette Hargrove
Selma Blairas Cecile Caldwell
Louise Fletcheras Helen Rosemond
Joshua Jacksonas Blaine Tuttle
Sean Patrick Thomasas Ronald Clifford
Swoosie Kurtzas Dr. Greenbaum
Christine Baranskias Bunny Caldwell
Tara Reidas Marci Greenbaum
Theo van de Sande