The 40-Year-Old Virgin (2005)

40-year-old Andy Stitzer (Steve Carell) has done quite a few things in his life. He's got a cushy job stamping invoices at an electronics superstore, a nice apartment with a proud collection of action figures and comic books, good friends, a nice attitude. But there's just one little thing he hasn't quite gotten around to doing yet--something most people have done by his age. Andy's never, ever, ever had sex. His friends at the store consider it their duty to help, but nothing proves effective enough until he meets Trish (Catherine Keener), a 40-year-old mother of three. Andy's friends are psyched by the possibility that "it" may finally happen...until they hear that Andy and Trish have begun their relationship based on a mutual no-sex policy.