Insecure

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.

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.

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. 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.

Issa finds herself at a crossroads in both her career and relationship. Molly spends an emotional day getting her parents’ will 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.

As she and her friends try to make time for each other no matter what, Issa looks back on all it took to get to where she is today.

Looking back at five memorable seasons of Insecure's messy relationships and hella personal growth, this documentary finds creator/star Issa Rae and others reflecting on the hit series.