Jason is currently working with his best friend Daniel (Miles Teller) at a publishing house designing book covers. Their friend Mikey (Michael B. Jordan), a young doctor who has been married to Vera (Jessica Lucas) since the end of college, comes to them after Vera requests a divorce. The three decide to go out to a bar and celebrate being single. The group meets up with Daniel's female wingman, Chelsea (Mackenzie Davis), as they try to get Mikey's mind off of his wife. Mikey meets a girl with glasses (Kate Simses), while Jason meets Ellie (Imogen Poots), and hits it off with her after teasing another man that was trying to buy her a drink. Mikey gets the girl's number, but puts off calling her, resolving to work it out with Vera. Jason sleeps with Ellie, but leaves her apartment in a hurry after jumping to the mistaken conclusion that she is a prostitute.