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 daughter of the principal of the private school that the three attend.

The movie received considerable criticism for its portrayal of teenagers in sexual situations.

The scene where Kathryn teaches Cecile Caldwell (played by Selma Blair) how to kiss, was voted 2nd in the list of "100 Greatest sexy moments" in the history of film [1], compiled by Channel 4.

The film later spawned a TV series called Manchester Prep, which was not picked up for broadcast, and two direct-to-video sequels, of which the first consisted of the series' pilot reworked to contain new scenes, harsher language and nudity.

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