Peter (Paul Rudd) needs a Sydney (Jason Segel) in his life. He has been told this by Zooey (Rashida Jones), the girl he plans to marry. She would, however, have preferred a less extreme case than this Sydney. Peter is a real-estate agent who is hopelessly, even touchingly, clueless when it comes to seeming the least bit cool. One of those really nice guys, who, when the chips are down, has no idea where to look, what to say, how to move or how to extricate himself gracefully from an impossible situation. He gets along great with women but has no male best friend and actually needs to find one to be best man at his wedding.