Each one of the film's title characters faced one of the comedies Apatow directed: The 40-Year-Old Virgin (2005), Knocked Up (2007), Superbad (2007), and Forgetting Sarah Marshall (2008).
Andy (Jeff Daniels) is a 41-year-old who desperately wants to lose his virginity. He lives with his teenage roomates, Scott (Jason Segel) and Seth (Jonah Hill). The two share a house together when they are not at school. They have no money and most of their belongings are tied to their bodies. Scott has a crush on a girl named Allison (Leslie Mann) who Andy likes. Andy hopes to be able to lose his virginity with Allison, but things do not go as he wishes. Through the course of the film, Andy tries to lose his virginity to seven girls, but is unsuccessful every time. Each experience makes Andy feel more depressed and awkward. This is the cause of his infertility in his 40's.
Andy finds himself in an awkward situation. Scott and Seth take their frustrations with Andy out on him by mistreating him. They leave him alone to take his frustrations out by having sex with his roommates. The four of them end up having sex. They hit the jackpot when they find themselves with a friend named Nadine (Sarah Hyland). Andy is ecstatic because Nadine is his type of girl. At the end of the day, he finds out that Nadine has not had sex in almost a year. This makes Andy feel really bad, and he begins to regret everything he has done. The movie ends with Andy seeing Allison again. He confesses to her his feelings, and she agrees to be his first.
Interspersed throughout are scenes of Andy talking about his past and his relationship with Sarah Marshall (who has been his friend and housemate for almost 20 years). He had a successful career as a standup comedian, then dropped out to pursue a music career. He was popular during his college years, a time in his life when he doesn't want to tell anyone about. One night, while drunk, he kissed a woman in the back of the club where he worked. He was devastated, and decided to give up comedy and start a family. He met Sarah in college, fell in love, and married her. She is the mother of their two children, whom he has never met. In the present, Sarah is dying of cancer, and Andy has been trying to get over the past and reconnect with his life. He finally decides to tell Sarah the truth. She is upset with him, and he in turn decides to tell his kids what happened, too.
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