College buddies chip in and promise that the group's last unmarried man will collect a cash pot. Seven years later, the kitty is worth $500,000 -- money Michael needs to pay a gambling debt. Problem is, the only other single guy is a hopeless womanizer!
Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates," before meeting Sydney Fife.