I Love You, Man (2009)

Friendless Peter Klaven goes on a series of man-dates to find a Best Man for his wedding. But, when his insta-bond with his new B.F.F. puts a strain on his relationship with his fiancée, can the trio learn to live happily ever after? - IMDb Editors

Peter Klaven's world revolves around his real estate work and Zooey, his soon-to-be fiancée. After he pops the question, she calls her best friends and they go into wedding planning mode. Peter has no male friends and that poses problems: will he turn out to be a clingy guy, and who will be his best man? Zooey, her friends, and Peter's brother Robbie offer help that results in awkward moments. Then, at an open house Peter's hosting, he meets Sydney, an amiable, low-key guy. They trade business cards, and Peter calls him to meet for drinks. A friendship develops that's great at first but then threatens Peter's engagement and career. Can guys be friends and couples be in love?

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. - Huggo