The 40 Year Old Virgin (2005)

Andy Stitzer, a 40-year-old virgin, still hasn';t had sex. He lives alone, collects action figures, plays video games, and his social life seems to consist of watching Survivor with his elderly neighbors. He lets his secret slip at a poker game with his buds from work. After the revealing all his friends are on a mission to help get him laid. Along the way Andy meets a nice mom: Trish who fall head over heels for each other.