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.

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.

It's 2016 and Darby's now hitched. As her marriage becomes increasingly distant, Darby reconnects with someone from her past who's determined to make amends for his callous behavior. Meanwhile, Sara and Jim struggle to reconcile their paradoxical visions for the future.

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.

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.

The girls head upstate to celebrate Mallory's engagement. At the cabin, Darby struggles to get through to Sara as their paths continue to diverge.

As he tries desperately to get his mind off Mia, Marcus joins Yogi and Kian for an ill-fated glamping trip.

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.

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.

As he juggles the challenges of his newfound career and family life, Marcus relishes a rare night out - and reflects on how far he’s come.

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.

Marcus Watkins begins to question his marriage as he develops a unique friendship with the magnetic Mia Hines.

Marcus rushes headfirst into a relationship with playwright Ola, but soon finds himself having trouble “performing.”

Marcus reconnects with Mia as he experiences complex emotions in the wake of Becca’s big reveal.

While in Michigan for their parent’s wedding anniversary, Marcus reignites an old flame and nurses the wounds of his failed relationship – as Ida contends with her own issues.

While juggling a causal relationship with an older woman, Marcus is forced to deal with his “daddy issues” - and some shocking news.

After an unexpected trip home, Mia experiences complicated feelings that may threaten her relationship with Marcus.

As 2020 disrupts life for everyone in his circle, Marcus makes great personal strides - but soon finds that all roads lead back to Mia.

As Marcus stumbles through the fallout from his former relationship, a reunion with Mia leads to a heated exchange – and a desperate reentry into the dating pool.