Film: My Best Friends Girl

My Best Friend's Girl is a 2008 romantic comedy starring Jason Biggs and Dane Cook. Dane Cook plays Tank, a cocky womanizer who is paid by recently dumped guys to take their ex-girlfriends on a date and be the biggest Jerkass possible in order to make them (the young men) look good by comparison. It works pretty well...until Tank is hired by his best friend and gets more than he bargained for.

Tropes include: