Last night I watch Cruel Intentions (1999). I have no idea why I decided to watch this silly adolescent film. I guess I can blame it on Amazon Prime--it was free!
Cruel Intentions follows Sebastian (Ryan Phillippe) who is the sexual terror of his prep school. He can have any girl he wants at will. Anyone except his stepsister, Katherine (Sarah Michelle Gellar), that is. Bored with so many easy conquests, he sets a challenge for himself--Annette Hargrove (Reese Witherspoon) who has vowed to remain a virgin until she finds true love. Sebastian makes a bet with Katherine that he can seduce Annette. If he fails, Katherine gets his sports car. If he succeeds, he gets a night with her. At first, Sebastian seems to have no chance, but, through a series of lies and manipulations, he softens Annette's reserve. Meanwhile, to help Katherine gain revenge on an ex-boyfriend, he agrees to bed the object of that boy's affection - a socially-inept and sexually naïve girl named Cecile (Selma Blair).
I do not recommend this movie unless you are looking for mindless entertainment.