One day he is playing poker with some of his co-workers when he reveals to them that he is 40 and is a virgin. The men David, Jay and Cal decide that they want to help him out. They convince him to have his chest waxed which Andy finds very painful. One of the men counsels him to just ask women that he likes questions and not reveal anything about himself so that they want to find more about him.
The first woman that Andy meets is played by Elizabeth Banks and her name is Beth and she works at a book store. The relationship does not work out well. Paula who is Andy's manager also hits on him and makes him feel uncomfortable.
He finally meets a woman named Trish who is played by Catherine Keener. She is a single mom and really likes Andy for who he is. They get along well and go on many dates. Trish even introduces Andy to her daughter and the two get along well. Problems erupt though when Andy believes that Trish wants to change who he is so he breaks up with her and goes to see Beth. Marla, Trish's daughter finally gets Andy to see how much her mom loves her and the two reunite.
Shelley Malil – who starred with Steve Carell in The 40-Year-Old Virgin – convicted of attempted murder in September for the gruesome stabbing of his girlfriend in San Diego. Malil stabbed ex-girlfriend Kendra Beebe more than 20 times. This marks the end to a terrible event that left Beebe with life long scars to remind her of the event. On Thursday Malil, 45, was sentenced to life in prison with the possibility for parole, reports NBC San Diego.