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 attractive 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 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.
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