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Insecure
Season 5

Insecure

10 episodes

Reunited, Okay?!
E01
Episode 12021-10-2432m

Reunited, Okay?!

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.

Growth, Okay?!
E02
Episode 22021-10-3129m

Growth, Okay?!

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.

Pressure, Okay?!
E03
Episode 32021-11-0728m

Pressure, Okay?!

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.

Faulty, Okay?!
E04
Episode 42021-11-1428m

Faulty, Okay?!

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.

Surviving, Okay?!
E05
Episode 52021-11-2125m

Surviving, Okay?!

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.

Tired, Okay?!
E06
Episode 62021-11-2827m

Tired, Okay?!

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.

Chillin', Okay?!
E07
Episode 72021-12-0529m

Chillin', Okay?!

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

Choices, Okay?!
E08
Episode 82021-12-1228m

Choices, Okay?!

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.

Out, Okay?!
E09
Episode 92021-12-1929m

Out, Okay?!

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.

Everything Gonna Be, Okay?!
E10
Episode 102021-12-2641m

Everything Gonna Be, Okay?!

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.