The intentions are cruel sometimes, and sometimes they are quite witty. Gellar plays one evil bitch. Her scheming, cocaine sniffing, and look is the backbone behind this picture from first time director Roger Kumble.

She makes a bet with her step-brother (Phillippe). It isn't your usual bet. This one involves seduction and manipulation. Phillippe is to try and sleep with Reese Witherspoon, the virginal daughter of Phillippe's high school Headmaster. If he wins, he gets Gellar, if he loses, she gets his car.

It's easy to tell this is a debut from Kumble, because he doesn't succeed in all of the story. While Phillippe is out on his conquest, Gellar has one of her own. She's trying to ruin her ex-boyfriend's new gal pal's (Selma Blair) reputation. Kumble does part of this quest and then ignores it in the latter stages. It wouldn't have been such a big deal had the movie not made Blair such a big character. Gellar's attempts to ruin Blair's rep is introduced early in the picture, so the audience expects to find out what happens, but we only get half the answer.