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Carl Peterson and Randy Dupree have been friends forever. But everything changes when Carl marries Molly Thompson and best man Dupree becomes the third wheel. Free-spirited Dupree's antics suddenly seem juvenile and Carl has to decide where his loyalty lies--with his new wife or his best friend. Still, when Carl discovers that Dupree is down on his luck, he invites his best buddy to move in until he's back on his feet. Unfortunately, Dupree isn't exactly Molly's idea of the perfect houseguest as the perpetual bachelor is really an overgrown kid.