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.

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.

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.