Comedy directed by John Hamburg. After becoming engaged to Zooey (Rashida Jones), the woman of his dreams, estate agent Peter Klaven (Paul Rudd) realises to his horror that he has no male friend close enough to be his best man at the wedding. Peter embarks on a series of bizarre and awkward 'man-dates' until he meets Sydney Fife (Jason Segel), with whom he instantly bonds. But the closer the two men get, the more Peter's relationship with Zooey suffers, until he is finally forced to choose between his fiance and his new best friend.