Andy and Trish's relationship grows. Andy runs into Beth and they soon leave for her apartment. Trish suggests that they postpone having sex, and Andy enthusiastically agrees. During Andy and Trish's first date, as they are about to have sex, they are interrupted by Trish's teenage daughter Marla. Jay attempts to quicken the process by tricking Andy into meeting a prostitute. Andy lands a date with Trish Piedmont, a woman he met on the sales floor. Andy tries to defend himself and declares his love for her, but she leaves in alarm and disgust.
Jay, who previously boasted of his promiscuity, gets into an argument with a customer after his girlfriend breaks up with him over his infidelity. When Andy discovers the hooker is a male transvestite , he insists that his friends stop trying to help him. By this time, Andy has sobered up and is having second thoughts. 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. Mooj stresses to Andy the importance of love in a relationship. Trish encourages Andy's dream of starting a business, suggesting they fund it by selling his collectibles. 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. David gives Andy his porn collection, encouraging him to masturbate. Andy chases after her on his bike, but collides with her car and flies through the side of a truck. Cal advises Andy to simply "ask questions", which he practices on bookstore clerk Beth, who quickly becomes intrigued by him. Andy runs into Beth and they soon leave for her apartment. Marla convinces Trish to make up with Andy. Trish is surprised but relieved, and they kiss. Andy returns to his apartment, where he finds Trish waiting for him. 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. David, obsessed with Amy, takes a vow of celibacy. Andy takes Marla to a group session at a sexual health clinic , where she reveals she is a virgin. David, after running into his ex-girlfriend Amy, has an emotional breakdown at work. 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. Marla later says that she knows Andy is a virgin, but agrees to let him tell Trish himself. Jay attempts to quicken the process by tricking Andy into meeting a prostitute. Andy begins to socialize and form friendships with his co-workers. Andy, trying to defend her against derision, admits that he is also a virgin but is disbelieved and ridiculed. Andy tries to defend himself and declares his love for her, but she leaves in alarm and disgust. Trish suggests that they postpone having sex, and Andy enthusiastically agrees.
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