Sex Ed Dolan is the 22nd episode of Season 1, it aired on May 8, 2014.
To get out of a night "tomcatting" with his boss, Ed, Nathan has Tom turn on the charm and share some common interests. But that only leads to Ed sleeping with Carol. After one night, Ed becomes clingy and Carol tries to figure out a way to leave him without hurting Nathan's standing at work. Carol's family is more than ready to provide suggestions to make Ed leave her, which mostly involve Carol being herself.