Cruel Intentions is a 1999 film starring Sarah Michelle Gellar, Ryan Phillippe, Selma Blair and Reese Witherspoon. It was loosely based on the film Dangerous Liaisons, itself based on the 18th century French novel Les liaisons dangereuses, but played with teenagers.
The plot concerns a bet made between Kathryn Merteuil, played by Gellar, and Sebastian Valmont, played by Phillipe. Sebastian must sleep with Annette Hargrove, played by Witherspoon, a virgin, and the daughter of the principal of the private school which the three attend.
The movie received considerable criticism for its portrayal of teenagers in sexual situations.