The 40-Year-Old Virgin

Andy Stitzer is a shy 40-year-old introvert who works as a stock supervisor at the electronics store Smart Tech. He gave up trying to have sex after various failed attempts and lives alone in an apartment with a collection of action figures and video games. When a conversation at a poker game with his co-workers, David, Jay, and Cal, turns to past sexual exploits, they figure out that he secretly is still a virgin. Andy is mortified upon discovering the next day that everyone else at work has learned about the secret, including their boss Paula, who is attracted to him and later privately offers to take his virginity. He almost quits work in humiliation before David consoles him and recommends trying again to have sex. David, Jay, and Cal become determined to help Andy achieve this. They all give differing advice on how to interact with women. David invites him to join them for a speed dating event and unsuccessfully tries to reconnect with his ex-girlfriend Amy there. Jay drags Andy to various social events, books a painful chest waxing appointment, and sets him up with a prostitute, which all end with embarrassing results. Cal advises Andy to be confident and to ask women questions instead of talking about himself. He practices this on a bookstore clerk named Beth, who quickly becomes intrigued by him. David gives Andy his pornography collection, encouraging him to masturbate. Andy eventually gets a date with a customer named Trish Piedmont. At the end of their first date, they almost have sex, but are interrupted by her 16-year-old daughter, Marla. Trish suggests they postpone having sex, and Andy enthusiastically agrees; they decide to abstain until their 20th date. Their relationship flourishes over the following weeks. She encourages Andy's dream of starting a business and helps fund it by selling his collectibles. After Marla argues with Trish over wanting birth control, Andy takes her to a group information session at a sexual health clinic, where she is mocked for being a virgin. Andy admits his virginity to defend her, earning him Marla's respect. Meanwhile, David suffers an emotional breakdown at work over his obsession with Amy, and takes a vow of celibacy. The breakdown prompts Paula to assign Andy his sales duties for the day, and she later promotes him to floor manager for his high sales quota. As Cal takes on Andy's previous role, he hires a woman named Bernadette to work at the store, hoping to match her with David so he can move on from Amy. After Jay's girlfriend, Jill, breaks up with him due to his infidelity, he concedes to Andy that sex can ruin a relationship. Following a reconciliation with Jill, Jay invites Andy and the others to a nightclub celebrating her pregnancy. Trish tries to initiate sex with Andy on their 20th date and becomes upset when he resists. They argue, and Andy leaves to meet his friends at a nightclub. He gets drunk and leaves with Beth to have sex at her apartment. Cal gets David and Bernadette to hook up, while Marla convinces Trish to reconcile with Andy. At Beth's, Andy sobers up and decides to leave without having sex, just as his friends arrive and encourage him to go back to Trish. Andy returns to his apartment to find Trish waiting for him. She has seen David's porn collection; he tries to explain, but she flees in alarm and disgust, fearing Andy may be a sexual deviant. While pursuing her on his bike, Andy collides with her car, flying through the side of a billboard truck. She rushes to his side, and Andy finally confesses that he is a virgin. Trish is relieved and accepting, and they profess their love for each other. They eventually marry in a lavish ceremony with everyone in attendance, having generated roughly $500,000 from the sales of his action figures to pay for it, before having sex for the first time. The film ends with a musical sequence where all the characters sing and dance to "Aquarius".