Insecure

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.

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, with help from Kelli, Molly spends an overwhelming day getting her parents' estate plan in order.

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

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 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.

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.

Still adjusting to newfound responsibilities, one of Issa's exes finds himself torn between two places, while an important woman in his life remains wary of his ability to be fully present back home.

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.

Pulling up to her ten-year college reunion in style as an alumni panelist, Issa's self-doubt quickly surfaces, while Molly – still reeling from her breakup – struggles to get out of her own head. As the crew takes the opportunity to reflect, old wounds remain tender.