John Tucker Must Die (2006)

Synopsis
Three teenagers two-timed by a local lothario decide to turn the tables on him in this romantic comedy. John Tucker (Jesse Metcalfe) is the big man on campus at his high school -- he's the captain and star player of the basketball team, he's got money, he's good-looking and charming, and he can have any girl he wants. However, the latter attribute is about to get him in serious trouble when three different girls at his school -- Heather (Ashanti), Beth (Sophia Bush) and Carrie (Arielle Kebbel) -- discover they've all been dating John at the same time. Determined to bring down the campus ladykiller, the girls devise a plan -- they pick a cute but socially clumsy girl who is new at school, Kate (Brittany Snow), and give her a crash course in stealing John's heart. Once Kate has John wrapped around her little finger, she's supposed to drop him like a bad habit and give him a taste of what heartbreak is really like. However, it seems that the early stages of the plan work a little too well, and John and Kate end up falling for each other for real. John Tucker Must Die also stars Jenny McCarthy, Penn Badgley, and Dan Payne. ~ Mark Deming, All Movie Guide