The film follows the story of an aspiring New York dramaturge who forms an unexpected connection with a divorced guy while crossing an unpleasant parting. Jessica James (Jessica Williams) is struggling to live in New York, paying her bills by teaching theater to children as part of a nonprofit program for children. Jessica is also struggling to get past the recent breakup of Damon, which eventually leads her to an unseen encounter with Boone (Chris O’Dowd), a man recently divorced. As Jessica and Boone cross the failures of previous relationships and their emotional luggage, they try to create a new story. The unexpected duo forms a special link and discovers how to go through difficult times in a post-relational universe obsessed with social media.