40 Year Old Virgin (2005)
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When Andy accidentally tells his work pals that he’s still a virgin at 40, the guys make it their duty to change that. Andy meets and falls for single mom Trish, and the boys think the deed is all but done. Only one problem: Andy and Trish start their relationship with a no-sex policy. Starring Steve Carell, Catherine Keener, Paul Rudd and Seth Rogan.