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."

Everybody has one—the sibling who is always just a little bit behind the curve when it comes to getting his life together. For sisters Liz, Miranda and Natalie, that person is their perennially upbeat brother, Ned. But as each of their lives begins to unravel, Ned's family comes to realise that Ned isn't such an idiot after all.