First Hit: There are some funny bits in this film along with some good serious truthful moments; however it felt long, repetitious, and overdone in parts.
Paul Rudd plays Peter Klaven a moderately successful real estate agent who has a dream of building a group of homes and stores on a bluff near downtown LA.
To finance this venture he must sell Lou Ferrigno’s home for which he has the exclusive listing. He is engaged to Zooey (played by Rashida Jones) who feels like she has hit the jackpot with Paul as her boyfriend.
As a boyfriend, Peter is thoughtful, kind, considerate, and pays attention to her. All her girlfriends think she’s so lucky but there is an underlying concern; Peter doesn't have any guy friends. The fact is that Peter doesn’t is the gist of the film. He and his fiancé decide that he needs to find some guy friends before the wedding or else the wedding party will be uneven.
In his quest to find a guy friend, he has a number of man dates. There are funny bits in some of these encounters. Then during an open house he is having for Lou’s home, he runs into Sydney (played by Jason Segel) who is blunt, insightful, and outspoken. They hit it off because in many ways they are opposite and they both love the band Rush.
Through a series of man dates, their relationship expands and eventually he asks Sydney to be his best man. However, Zooey doesn’t like that Peter is less available and pays less attention to her now that he has a guy friend to hang out with.
I found the repetition of scenes, like Peter attempting to come up with a nick name for Sydney, to be tiring and overplayed. The direction of the unevenness and the upsides of this film the responsibility of Director John Hamburg and co-writer Larry Levin. Rudd was OK as Peter; while Segel was the strongest consistent character as Sydney. I found the couple Jon Favreau and Jaime Pressly as Zooey’s best friend and husband, to be overplayed, unrealistic, and boorish.
Overall: This film’s unevenness took away from the truly funny parts and in the end, this film felt very long. It might have been better to cut 20 minutes from it by reducing extraneous and repetitive scenes.