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.

After Darby runs into an old flame and his new girlfriend, her best friend Sara, who's eager to bail on her long-term boyfriend Jim's family obligation, convinces Darby to join her at a coworker's rooftop party. After hours spent stalking her ex's new girl on social media, she winds up connecting with an overeager, romantically bruised.

After a "serendipitous" reunion, Darby and Augie find themselves falling into a comfortable, full-blown relationship (again). However, Darby is soon left wondering whether "comfortable" is enough.

Now an overextended gallery owner, Darby relishes some much-needed alone time during a friend's New Year's Eve wedding. The ceremony fosters a new appreciation for her perfectly imperfect life.