Following her parents' divorce, Darby Carter struggled to make connections as an adolescent and, later, as a NYU student, until she meets Augie Jeong at a karaoke party. After their whirlwind night together and several days spent waiting by the phone for Augie's follow-up "WYD" text, Darby quickly finds herself in a comfortable, full-blown relationship.

A year later, Darby's life and career feel stagnant. When sparks fly with Bradley, her former boss who's recently divorced and highly successful, Darby feels pressure to revisit her half-baked dream of becoming a photographer, but soon gets swept up into girlfriend duties instead.