In I Love You, Man, a comedy from John Hamburg (Along Came Polly, co-writer of Meet The Parents, Meet The Fockers, Zoolander), Peter Klaven (Paul Rudd, Knocked Up The 40 Year Old Virgin) is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, (The Offices Rashida Jones), 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, before meeting Sydney Fife (Jason Segel, Forgetting Sarah Marshall), a charming, opinionated man with whom he instantly bonds. But the closer the two men get, the more Peters relationship with Zooey suffers, ultimately forcing him to choose between his fiancée and his new found bro, in a story that comically explores what it truly means to be a friend.

Peter has just gotten engaged to Zooey, and everything is going well for him. That is until he slowly realizes that he does not have any friends that could serve as his best man. Peter seeks the advice of his brother on how to meet new people to become his potential best man. After several bizarre man-dates, Peter gives up completely and focuses his efforts on trying to sell a house that belongs to Lou Ferrigno. Determined to sell the house, Peter holds an open house for prospective buyers. There he meets Sydney Fife, a very honest and laid back investor who takes a liking to Peter. While conversing with Sydney, Peter learns that Sydney is a very blunt and honest person. They hit it off and trade business cards. When Peter finally gets the guts to call Sydney back, he leaves a very embarrassing message for him. Later in front of Zooey's girlfriends, Sydney calls back and Peter and Sydney go on a man-date. Peter who's usually a girly kind of guy who hates drinking, gets pretty drunk with Sydney. They go on to become best friends over the course of the months leading up to Peter's wedding, Peter asks Sydney to be his best man. Sydney borrows money from Peter. When Zooey confronts Peter on his lies about the money, they temporarily split up. Peter finds out that the money went towards a series of billboard ads across town. Peter finds the billboards ridiculous, as they don't fit with his professional personality. He confronts Sydney to get him to have the signs taken down and to get his money back, which Sydney promises to do. Peter and Sydney decide to end their relationship because of this conflict. However when Peter gets back to the office, he finds out that the ads worked; not only did he receive more clients, he sold the Ferrigno house. While Peter feels bad that he ended the relationship with Sydney, he doesn't re-invite to the wedding. Before the wedding, Zooey sees Peter is upset about Sydney, so she calls and invites Sydney (who is already on his way) to the wedding. Just before the Vows are to be taken, Sydney makes a dramatic entrance, they explain their platonic love for each other, and Sydney assumes the role of Best Man.

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