#2. The 40-Year-Old Virgin (2005)
Andy Stitzer (Steve Carell) is an amiable single guy who works at a big-box store. Living alone, 40-year-old Andy spends his free time playing video games and curating his action-figure collection. Despite his age, Andy has never had sex, so his friends, including the laid-back David (Paul Rudd), push Andy towards losing his virginity. While attempting to get over his awkwardness around female customers, Andy meets local shop owner Trish (Catherine Keener), and they begin a tentative romance.