Cruel Intentions

1999 · 1h37 · Film

Directed by Roger Kumble

Starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair, Louise Fletcher, Joshua Jackson, Eric Mabius, Sean Patrick Thomas, Swoosie Kurtz, Christine Baranski

Ideal when you feel… Romantic

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.

Updated July 22, 2026

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