The 40 Year Old Virgin

 (2005)

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The 40 Year Old Virgin
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Plot 1
'Goaded by his buddies, a nerdy guy who\'s never \"done the deed\" only finds the pressure mounting when he meets a single mother.'
Plot 2
The 40-Year-Old Virgin is a 2005 comedy film written and directed by Judd Apatow and co-written by the film's lead star, Steve Carell, though the film itself features a great deal of improvised dialogue. It also stars Catherine Keener, Romany Malco, Seth Rogen (who was also the co-producer) and Paul Rudd, as well as Leslie Mann (Apatow's wife) and Nancy Walls (Carell's wife) in small roles.

Source: Wikipedia