The 40 Year Old Virgin (2005)
Genre: Comedy, Romance
Director: Judd Apatow
Starring: Steve Carell, Catherine Keener, Paul Rudd
Andy at the age of 40 have not yet had sex. He lets his secret slip at poker game with his buds from work. After revealing all his friends are on a mission to get him laid. Along the way Andy meets a nice mom: Trish who fall head over heels for each other.