Peter Klaven is a successful real estate agent, who, upon getting engaged to the woman of his dreams, Zooey, discovers to his dismay that he has no male friend close enough to serve as his best man. Peter immediately embarks on a series of bizarre and awkward 'man-dates' to find such a friend, before meeting Sydney Fife, a fun-loving, charismatic man - just Peter's oppposite - with whom he instantly bonds. But the closer the two men get, the more Peter's relationship with Zooey suffers, ultimately forcing him to choose between his fiancee and his new found 'bro', in a story that comically explores what's at the core of male friendship and what it truly means to be a friend.