Looking back at five memorable seasons of Insecure, this documentary finds creator/star Issa Rae and others reflecting on the hit series.

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.

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.

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

A much-needed girls' night puts things into perspective for Issa and her crew.

A distracted Issa mulls over difficult choices in both work and love, while Molly finds a comforting audience 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.

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