Fortysomething Cal Weaver is living the dream: good job, nice house, great kids, and marriage to his high school sweetheart. So when Cal learns that she has cheated on him and wants a divorce, his 'perfect' life quickly unravels. Cal, who hasn't dated in decades, stands out as the epitome of un-smooth, so handsome player Jacob Palmer takes him on as wingman and protege.

Title from disc label. Special feature: Steve and Ryan walk into a bar; The player meets his match; Deleted scenes. Videodisc release of the 2011 motion picture.