The 40-Year-Old Virgin (2005)

Andy is a 40-year-old store clerk with a rather unusual secret - he's still a virgin. When his coworkers uncover the truth, they help him navigate the complexities of modern dating while concealing his inexperience. Director Judd Apatow enlists the comedic brilliance of Steve Carell, Paul Rudd and Seth Rogen, delivering an unforgettable comedy with iconic scenes that guarantee an incredibly entertaining experience.