Matteson Perry is a Nice Guy. He remembers birthdays, politely averts his eyes on the subway, and enjoys backgammon. He's a serial monogamist, and he's never asked a stranger out. But when the girl he plans on marrying dumps him, he decides to turn his life around. He comes up with The Plan: 1. Be single for a year. 2. Date a lot of women. 3. Hurt no one's feelings. He is not out to get revenge, or even to become The Pickup Artist; he just wants to disrupt his pattern, have some fun, and discover who he is when he is unattached (much like a male Taylor Swift). A quick-witted Everyman, Matteson throws himself into the modern world of courtship and digital dating, only to discover that the even the best-laid plans won't necessarily get you laid.