The 40-Year-Old Virgin (2005) is a hilarious comedy about Andy Stitzer (Steve Carell), a middle-aged man who has never had a romantic relationship. When his co-workers discover his secret, they set out to help him find love and lose his virginity.
From Wikipedia
The 40-Year-Old Virgin is a 2005 American romantic sex comedy film directed by Judd Apatow, who produced the film with Clayton Townsend and Shauna Robertson. It features Steve Carell as the titular 40-year-old virgin Andy, an employee at an electronics store. Paul Rudd, Romany Malco, and Seth Rogen play co-workers who resolve to help him lose his virginity, and Catherine Keener stars as Andy's love interest, Trish.