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A man is being driven crazy by his shiftless best friend, just as the layabout starts making nice with his wife and neighbors in this comedy. Carl and Molly (Matt Dillon and Kate Hudson) are a thirtysomething couple who have just gotten married and are settling down into a cozy new home in a quiet neighborhood. While Carl and Molly are happy with their new digs, Carl's best friend, Randy Dupree (Owen Wilson), is not content with his living arrangements. Dupree has all but made a career out of avoiding work, responsibility, and commitment, and while his charm usually manages to keep him afloat, when he loses his job, his apartment, and his car. Carl can't bear to see Dupree in such dire circumstances, and tells Dupree he can stay on their couch until he can get things straightened out. But while Carl was expecting Dupree to stay for a few days, it soon becomes obvious to both him and Molly that their guest has no intention of moving out anytime soon, and while the likable freeloader starts working his charm on Molly, their neighbors, and their friends, Carl soon finds himself at the end of his rope with his best man and childhood buddy. You, Me and Dupree also stars Amanda Detmer, Seth Rogen, and Michael Douglas as Molly's father.