Kathryn (Sarah Michelle Gellar, "Buffy") and Sebastian (Ryan Phillippe) are super rich teenagers and step siblings. Their idea of fun is making a wager on if Sebastian can take the virginity of the new headmaster's daughter Annette (Reese Witherspoon, Election). The prize? Sebastian gets to sleep with Kathryn if he wins, while she gets his expensive car if he's unsuccessful.

Naïve Cecile (Selma Blair, Amazon High, Pretty Persuasion) is new in town and going out with Kathryn's ex-boyfriend. Kathryn has a plan to get back at her and volunteers to teach her how to French kiss. She explains, "OK, I'm going to stick my tongue in your mouth, and when I do that, I want you to massage my tongue with yours."

Just how many lives will Kathryn and Sebastian disrupt and corrupt?

Gellar and Blair won the MTV Movie Award for "Best Kiss" for this scene.