The 40 Year Old Virgin

The 40YearOld Virgin is a 2005 American comedy film written, produced and directed by Judd Apatow, about a middleaged mans journey to finally have sex. It was cowritten by its star, Steve Carell, though it features a great deal of improvised dialogue. The film was released theatrically in North America on August 19, 2005 and was released on regionDVD on December 13, 2005. It is the directorial debut of Judd Apatow, who would go on to direct such successful films as Knocked Up, Funny People, This is 40, and Trainwreck and Seth Rogens first comedy film, since playing a cameo in the 2004 film Anchorman The Legend of Ron Burgundy.

The group resolves to help Andy lose his virginity. Throughout the next several days, the groups efforts prove to be unsuccessful, partly because all three men give Andy different and sometimes contradictory advice. They take him to have his chest waxed, which he gives up halfway. Cal advises Andy to simply ask questions when talking to women, which makes Andy seem mysterious. His advice proves to be the most helpful, when Beth Elizabeth Banks, a bookstore clerk, takes a liking to Andy. Andy starts to open up, and begins to form friendships with his coworkers. After running into his exgirlfriend Amy in a speeddating event, David, who is still obsessed over her, has an emotional breakdown while making a sale. Store manager Paula Jane Lynch sends him home and promotes Andy to fill in for him.Jay attempts to quicken the process by hiring Andy a prostitute. When Andy discovers she is a transvestite, he confronts his friends and tells them that he will manage a date with a woman on his own. Andy lands a date with Trish Piedmont Catherine Keener, a woman he met on the sales floor. During Andy and Trishs first date, as they are about to have sex, they are interrupted by Trishs teenage daughter Marla Kat Dennings. Andy prepares to tell Trish he is a virgin, but Trish suggests that they postpone having sex. Andy enthusiastically agrees they decide to postpone it to the 20th date. At work, Paula is impressed by Andys salesmanship and promotes him to floor manager. ........

Source: Wikipedia