The film traces the misadventures of buddies J.D. (Jack Black) and Wayne (Steve Zahn), who begin to suspect that their best friend, Darren Silverman (Jason Biggs), is going to allow himself to be badgered into marrying Judith (Amanda Peet), a woman he doesn't love. They decide to reunite him with his long lost love from their school days (Amanda Detmer) -- even if they have to kidnap Judith to do it.