CRUEL INTENTIONS (1999)

In the game of seduction, there is only one rule: Never fall in love.

Annette (Reese Witherspoon) unwittingly becomes a pawn in Sebastian's (Ryan Phillippe) and Kathryn's (Sarah Michelle Gellar) deliciously diabolical wager of sexual conquest when she writes an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. However, Sebastian gets more than he bargained for as he attempts to woo Annette into his bed.