Andy (Steve Carell) is 40 years old. He has a high-paying job and lives a quiet life. However, when he accidentally revealed that he was still a virgin during a chat with his friends, trouble came. His friends are most anxious to introduce a girl to Andy so that he can get rid of his virginity as soon as possible. Although Andy himself is also anxious, sometimes the more anxious he is, the more confused he becomes. Friends arranged for Andy to meet girls at the bar, but Andy couldn't take the girls he met for a ride like others because he couldn't drive. Every date was full of jokes and Andy made a fool of himself. Andy met Tracy (Catherine Keener), a single mother with three children, and the two quickly fell in love. Can Andy get rid of his virginity this time?