The 40 Year Old Virgin
Tags: comedy, adult comedy, cute, flashback, humor, romantic, entertaining

Plot synopsis:
Andy Stitzer (Steve Carell) is a 40-year-old virgin who lives alone, collects action figures, plays video games, and whose social life seems to consist of watching Survivor with his elderly neighbors. He works in the stockroom at SmartTech, an electronics store. When a friend drops out of a poker game, Andy's co-workers David (Paul Rudd), Cal (Seth Rogen), Mooj (Gerry Bednob), and Jay (Romany Malco) reluctantly invite Andy. At the game, when conversation turns to past sexual exploits, the group learns that Andy is still a virgin.
The group resolves to help Andy lose his virginity. Throughout the next several days, the group's 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 co-workers. After running into his ex-girlfriend Amy in a speed dating 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 the hooker is a male 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 Trish's first date, as they are about to have sex, they are interrupted by Trish's 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 Andy's salesmanship and promotes him to floor manager.
As Andy's 20th date draws closer, his friends begin to deal with the consequences of their lifestyles. David, still spiraling in his obsession with Amy, has become disillusioned with sex and has taken a vow of celibacy. Cal, worried about him, hires Bernadette (Marika Dominczyk), an attractive woman, to fill in for Andy. Jay gets into an argument with an obnoxious customer (Kevin Hart). He confides with Andy that his girlfriend Jill learned of his infidelity and broke up with him. Andy comforts Jay, who says that sex can ruin a relationship. Jill later decides to take Jay back (she is pregnant, and her misgivings about Jay as a father figure were what had spurred the breakup).
Andy and Trish's relationship grows, and Trish suggests that Andy sell his collectible action figures, which will earn him enough money to open his own store. Later, Andy takes Marla to a sexual health clinic, where Marla reveals herself to be a virgin. The counselor (Nancy Carell) remains sympathetic, while the other patients in the clinic laugh at Marla. Andy admits that he is a virgin as well, but only gains ridicule himself. On the way back to Trish's house, Marla tells Andy that she has known he is a virgin for a while. She promises to let Andy tell this to Trish by himself.
On their 20th date, Andy is still reluctant about sex and resists Trish, upsetting her. An argument ensues, in which Andy accuses Trish of pushing him into changing his life against his will. He leaves for the nightclub where Jay is celebrating his girlfriend's pregnancy. David finally relinquishes his celibacy and hooks up with Bernadette. Andy gets drunk and, after running into Beth, goes to her apartment with her. Marla convinces Trish to go and make up with Andy. By this time Andy has sobered up and, after witnessing Beth's methods of foreplay, he starts to have second thoughts. His friends arrives and encourage Andy to go back to Trish.
They leave together (except for Cal), and Andy returns to his apartment, where he finds Trish waiting for him. He attempts to apologize, but Trish, having found various suspicious items in his apartment, is now afraid that Andy may be some sort of sexual deviant. Andy tries to convince her otherwise and declares his love for her, but she leaves in alarm and disgust. Andy chases after her on his bike, but collides with her car and flies headlong into the side of a truck. Trish rushes to him in concern, and he finally confesses to her that he is a virgin. She is surprised to learn that this is the reason behind his strange behavior, as she does not consider it to be important, and they kiss.
Later, Andy and Trish are married in a lavish ceremony with everyone in attendance, with a sidelong mention of Andy's action figures having sold for half a million dollars. Afterwards, they consummate the marriage over a period of two hours and three minutes, transitioning into a musical scene where the characters sing and dance to "Aquarius/Let the Sunshine In".