Peter Klaven (Paul Rudd), a big-time real estate salesman, just got engaged to Zooey Rice (Rashida Jones), a stunning girl who co-owns a boutique called ZHD with best friends Hailey (Sarah Burns) and Denise (Jaime Pressly). Zooey is ecstatic about the engagement and calls her friends to tell them about it, but Peter does not seem to have anyone special he’d like to share the good news with. At Peter's parents’ (J.K. Simmons and Jane Curtin) house, it comes out that Peter is actually a "girlfriend guy," and his guy friends when he was growing up "fell by the wayside." After overhearing Zooey's friends tell her that they are concerned Peter does not have any friends, Peter realizes he needs to find some male friends in order to have a best man for his wedding. Peter seeks the advice of his younger, gay brother Robbie (Andy Samberg) on how to meet platonic guy friends and how to take them on man-dates.
Peter's first attempt is to hang out with Barry (Jon Favreau), Denise's husband, for poker night with the guys. It ends horribly when, after chugging too many beers, Peter projectile vomits all over Barry, who already isn't fond of Peter to begin with. Robbie then sends Peter out with a guy from his gym for a soccer game. That does not last long, since the man angers fans at the game and has a very high-pitched voice. Peter's mother tries next by sending him to dinner with a man named Doug Evans (Thomas Lennon) who just moved to L.A. Against Robbie's advice, Peter goes to dinner with Doug, and it ends awkwardly with a deep tongue kiss, revealing Doug's homosexuality. Peter seeks man-dates online and finds Mel, who represented himself as a young man on his online profile, but is actually an old man.
With all these failed attempts, Peter decides to give up, but during an open house at Lou Ferrigno's, he meets Sydney Fife (Jason Segel). They instantly hit it off when Sydney gives a play-by-play of a potential buyer farting. Because of Sydney's honesty, the two men exchange business cards. When Peter calls Sydney he leaves a very embarrassing voice mail, but when Sydney calls him back they decide to go out for drinks.
