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.

Feeling empowered after her experience with Danny, Darby embarks on a noncommittal hookup bender, until she falls for up-and-coming chef Magnus. The new couple seem to be a fairytale match until Darby scores a career win while Magnus faces a setback.

When a therapist encourages her to address her fear of rejection, Darby recalls being 15 and applying to boarding school to get her parents' attention. When she's stranded there for Thanksgiving break, an encounter in the dining hall plunges young Darby into a blissful week with too-cool-for-school Luke Ducharme. But Luke becomes aloof when the student body returns to campus.

When Darby has a medical scare, her overbearing mom, Claudia, comes to town to help. As mother-daughter tensions rise, we learn that Claudia's past relationship struggles may have rubbed off on Darby. Despite their differences, the two try their best to connect.

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.