Wayne (Steve Zahn) and J. D. (Jack Black) are best friends of Darren Silverman (Jason Biggs). They do everything together and have since they were in grammar school. They even have a band together, tributing their favorite star of all time, Neil Diamond. But when Darren gets engaged to a snobby psychologist named Judith (Amanda Peet), Wayne and J. D. do not approve! His new flame is selfish and controlling, and wants Darren to drop his two oddball buddies. So, Wayne and D. J. set out to "save" Darren from Judith and attempt to get him to fall back in love with his old girlfriend, Sandy (Amanda Detmer). They must act fast, however, because Sandy is about to become a nun!