At her ten-year college reunion, Issa's self doubt quickly surfaces, while Molly struggles to get out of her own head.

Despite her now thriving business, Issa struggles to find her footing and turns to an old friend for support. Meanwhile, Molly contemplates jumping back into the dating pool.

Eager to embrace newfound responsibilities, one of Issa's exes finds himself torn between two places.

Issa and her new man tread awkward waters at a work-related social event. Meanwhile, Molly juggles multiple suitors, and Issa plays defense against online attacks about her business.

A family emergency finds Molly stretched thin between taking care of loved ones, staying on top of work, and zeroing in on her own perceived shortcomings. As a hectic day unfolds, Issa and her new man grow closer than ever.

A distracted Issa mulls over work and love as she stumbles through the consequences of her falling out with a colleague. Meanwhile, Molly still struggling to cope with family matters- finds comfort in an unlikely source.

A long overdue girls' night filled with self-reflection and real talk puts things into perspective for Issa and her friends.

At a crossroads in her career, Issa weighs the pros and cons of two viable paths while simultaneously contemplating an important personal next step. Meanwhile, Molly spends an overwhelming day getting her parents' estate plan in order.

At a friend's going away party, Issa navigates unresolved feelings. After spending the day letting loose with her new man, Molly opens up about her fears.