The 40 Year Old Virgin (2005)

Andy Stitzer is a 40-year-old virgin who lives alone, his apartment filled with his collection of action figures and video games. At a poker game with his co-workers David, Cal, Mooj and Jay, when conversation turns to past sexual exploits, they learn that Andy is still a virgin, and resolve to help him lose his virginity.

The men give Andy various and sometimes contradictory pieces of advice, both on his appearance and how to interact with women. Cal advises Andy to simply “ask questions”, which he practices on bookstore clerk Beth, who quickly becomes intrigued by him. David gives Andy his porn collection, encouraging him to masturbate. Mooj stresses to Andy the importance of love in a relationship.

Andy begins to socialize and form friendships with his co-workers. David, after running into his ex-girlfriend Amy, has an emotional breakdown at work. Store manager Paula promotes Andy to fill in for him.

Jay attempts to quicken the process by tricking Andy into meeting a prostitute. When Andy discovers the hooker is a male transvestite, he insists that his friends stop trying to help him. Andy lands a date with Trish Piedmont, 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. Trish suggests that they postpone having sex, and Andy enthusiastically agrees.

Andy’s friends begin to encounter the consequences of their lifestyles. David, obsessed with Amy, takes a vow of celibacy. Jay, who previously boasted of his promiscuity, gets into an argument with a customer after his girlfriend breaks up with him over his infidelity. Jay concedes to Andy that sex can ruin a relationship.

Andy and Trish’s relationship grows. Trish encourages Andy’s dream of starting a business, suggesting they fund it by selling his collectibles. Andy takes Marla to a group session at a sexual health clinic, where she reveals she is a virgin. Andy, trying to defend her against derision, admits that he is also a virgin but is disbelieved and ridiculed. Marla later says that she knows Andy is a virgin, but agrees to let him tell Trish himself.

On the couple’s twentieth date, the limit they agreed for their abstinence, Andy is still resistant, which upsets Trish. Trish demands he explain his reticence, and Andy accuses her of trying to change him against his will. He leaves for a nightclub where he meets his friends, gets drunk and praises them for encouraging him to have sex. Andy runs into Beth and they soon leave for her apartment. Marla convinces Trish to make up with Andy. By this time, Andy has sobered up and is having second thoughts. His friends arrive and encourage him to go back to Trish.

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 defend himself 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 through the side of a truck. Trish rushes to his side, and Andy confides that he is a virgin as explanation for his behavior. Trish is surprised but relieved, and they kiss.

Later, Andy and Trish are married in a lavish ceremony with everyone in attendance, with a sidelong mention that Andy’s action figures sold for over half a million dollars. Afterwards, they consummate the marriage, the aftermath of which transitions into a musical scene where the characters sing and dance to “Aquarius/Let the Sunshine In”.

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