Andy (Steve Carell Steve Carell) is 40 years old and leads a quiet life with a well-paid job. However, trouble came when he inadvertently revealed that he was a virgin when he was chatting with his friends. What his friends are most anxious about is how to introduce a girl to Andy so that he can get rid of his virginity as soon as possible. Although Andy himself is worried, sometimes the more anxious he is, the more chaotic he is. The friends arranged for Andy to go to the bar to meet the girl, but Andy couldn't take the girl he knew for a ride like everyone else, because he couldn't drive yet. Every date is full of jokes and Andy is full of jokes. Andy meets Trish, a single mother with three children (Katherine Keener Catherine Keener), and the two quickly fall in love. Can Andy get rid of his virginity this time?