The 40 Year Old Virgin (2005)
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Synopsis: Andy at the age of 40 still hasn’t had sex. He lets his secret slip at a poker game with his buds from work. After the revealing all his friends are on a mission to help get him laid. Along the way Andy meets a nice mom, Trish, and they fall head over heels for each other.
Director: Judd Apatow
Writers: Judd Apatow, Steve Carell
Stars: Steve Carell, Catherine Keener, Paul Rudd