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.