Andy Stitzer, the 40-year-old stock supervisor at a Smart Tech electronics store in Studio City, California, lives a quiet and solitary life. One day his co-workers, David, Jay and Cal, need another person for their after-hours poker game at the store, and although they consider Andy odd, they invite him. After the game, the talk turns to sex, and Andy is asked to share a raunchy story from his own life. Andy awkwardly attempts to oblige, but when he remarks that a woman’s breasts feel like a bag of sand, the other men realize that Andy is a virgin and vow to take him under their wing. The next morning, Andy goes to work and discovers to his horror that everyone at the store knows his secret. David, who is still lovelorn over a faithless ex-girl friend with whom he broke up two years earlier, draws Andy into his confidence and persuades him to go out with the guys that weekend. That night, Andy thinks back over his youthful experiences with women, all of which were so disastrous that he eventually gave up on sex. When the weekend comes, the men go to a bar to look for women, and Andy leaves with the drunken Nicky, who takes him for a terrifying ride before crashing the car and throwing up on him. The following day, an attractive woman named Trish comes into the store, and although Andy is not a salesperson, his co-workers push him into waiting on her. Trish has a store across the street, where she sells other people’s possessions over the Internet. She and Andy have a natural rapport, but Andy hardly knows how to react when she gives him her phone number. After work, the guys get the normally teetotalling Andy drunk and advise him to acquire some sexual experience before pursuing Trish. With the encouragement of his new friends, Andy submits to excruciating chest waxing, attends a “speed dating” event and tries unsuccessfully to masturbate to David’s pornographic videos. The guys even arrange a date for Andy with a prostitute who turns out to be a transvestite. Finally, Andy works up the nerve to ask Trish for a date, and she happily accepts. Andy does not drive, so Trish picks him up, and after dinner they return to her apartment and prepare to go to bed together. While Trish is out of the room, Andy tries to figure out how to use a condom, but the mood is broken when Trish’s teenage daughter, Marla, walks in with her boyfriend. The evening ends abruptly, but Andy resolves to see Trish again and tell her the truth. On their next date, before Andy can bring up the subject of his virginity, Trish tells him that she has three daughters and a grandchild. She then proposes that they keep their relationship platonic for the time being. Andy is delighted with the suggestion, and they agree to postpone sex until they have been on twenty dates. With the pressure of intimacy removed, Andy and Trish’s relationship thrives. Andy’s career also advances, as store manager Paula, who has made her own sexual interest in Andy known, makes him a salesperson and eventually promotes him to floor manager. One night, Andy confides his dream of opening his own stereo store, and Trish offers to help him raise the money by selling the valuable collection of mint-condition action figures he has owned since he was a boy. When Marla insists on going to a family planning clinic to learn about birth control, Andy offers to accompany her. During a sex education class, Marla is teased by the other teenagers for being a virgin, and Andy announces that he is also a virgin. On the way home, Marla promises to keep his secret from her mother. On the night of his twentieth date with Trish, Andy is suddenly overwhelmed by all the changes Trish has brought to his life and picks a fight with her. He then goes to a bar, where Jay is throwing a party to celebrate his girl friend’s pregnancy. Andy gets drunk and goes home with Beth, who works in a bookstore near Smart Tech. Beth is wild and sexually uninhibited, but Andy quickly loses interest and leaves. When he returns home, he finds Trish, who had come over to make up with him, inspecting David’s pornography collection with disgust. Andy declares his love, but Trish runs out and drives away, with Andy in pursuit on his bicycle. After chasing Trish through traffic, Andy crashes through a moving billboard, and when Trish rushes to his side, he confesses, “I’m a virgin. I always have been.” Andy and Trish marry, and make rapturous love on their wedding night.