- Jesse Metcalfe as John Tucker
- Brittany Snow as Kate
- Sophia Bush as Beth
- Ashanti as Heather
- Arielle Kebbel as Carrie
Kate is the new girl in school. She catches John Tucker dating three different girls at once: Carrie - the smart girl, Heather - the cheerleader, and Beth - the activist slut; none of them are aware that they are not the only girl in John's heart. Kate, having been raised by a single mother, has seen the pain caused by playboys like John Tucker, and she won't stand idly by. Together with the three jilted ex-girlfriends, they hatch a plan to teach John a lesson. Things rarely go as planned, especially when Kate starts to think that she might be falling for John herself.
Year: 2006
