The 1st season of Happy Endings follows a group of six twentysomething friends trying to make it in Chicago. Relationships evolve as they try to figure out who keeps what friends following a breakup, while Dave (Zachary Knighton), after being left at the altar by Elizabeth (Elisha Cutbert), finds some consolation in manning a food truck. Meanwhile, Jane Eliza Coupe considers her marriage to Brad ({$Damon Wayons Jr.), and Penny (Casey Wilson) tries to make new friendships.