Plot: After eight months of dating, realtor and aspiring developer Peter Klaven asks entrepreneur Zooey Rice to marry him, she who says yes. It isn't until then that they both realize that while Zooey has a plethora of female friends to populate the wedding party - with Denise and Hailey, her business partners, being her closest friends - Peter has no real male friends as he has always nurtured his female relationships. Who he previously assumed were his male friends he realizes now are more acquaintances or associates. Even within his family, he is closer to his mother, Joyce - who Zooey believes is his best friend - than he is to his father, Oswald, or younger gay brother, Robbie. To overcome the problem of who will be his best man, Peter goes on a quest for a bromance. This task is difficult for unassuming Peter, who really doesn't know how to deal with men in a true friendship. After several missteps with potential bros, Peter finally meets financial investor Sydney Fife at one of his open houses. Sydney is straightforward and perceptive but an overgrown adolescent in his personal life. Still, Peter and Sydney bond. As Sydney becomes a bigger part of Peter's life, Peter has to figure out how to balance his life with Zooey and his life with Sydney, the two who may have their own issues in what the other means in Peter's life.
Alternative Plot: As his wedding day approaches, Peter Klaven (Paul Rudd) realizes he has no one to act as his best man. Through a series of "man-dates," he finds Sydney Fife (Jason Segel), and the pair become instant friends. But as Peter's "bro-mance" with Sydney grows stronger, it threatens his relationship with his fiancee (Rashida Jones), forcing Peter to make a choice.
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