Insecure

Season 5

10 episodes 6 seasons

Release Date

Premiered

Insecure Season 5 released on October 24, 2021.

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Episodes

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S05E01 Aired October 24, 2021

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.

S05E02 Aired October 31, 2021

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.

S05E03 Aired November 07, 2021

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.

S05E04 Aired November 14, 2021

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.

S05E05 Aired November 21, 2021

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.

S05E06 Aired November 28, 2021

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.

S05E07 Aired December 05, 2021

Chillin’, Okay?!

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

S05E08 Aired December 12, 2021

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.

S05E09 Aired December 19, 2021

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.

S05E10 Aired December 26, 2021

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.