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Insecure

Creator Issa Rae (The Misadventures of Awkward Black Girl) stars as Issa Dee, who struggles to navigate the tricky professional and personal terrain of Los Angeles along with her best friend Molly (Yvonne Orji).

Season 5 Episode Guide

10 Episodes 2021

Episode 1

Reunited, Okay?!

Sun, Oct 24, 2021 32 mins

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

Insecure Season 5 Reunited, Okay?!

Episode 2

Growth, Okay?!

Sun, Oct 31, 2021 28 mins

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.

Insecure Season 5 Growth, Okay?!

Episode 3

Pressure, Okay?!

Sun, Nov 7, 2021 28 mins

Eager to embrace newfound responsibilities, one of Issa's exes finds himself torn between two places.

Insecure Season 5 Pressure, Okay?!
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Episode 4

Faulty, Okay?!

Sun, Nov 14, 2021 28 mins

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.

Insecure Season 5 Faulty, Okay?!

Episode 5

Surviving, Okay?!

Sun, Nov 21, 2021 25 mins

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.

Insecure Season 5 Surviving, Okay?!

Episode 6

Tired, Okay?!

Sun, Nov 28, 2021 26 mins

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.

Episode 7

Chillin', Okay?!

Sun, Dec 5, 2021 28 mins

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

Insecure Season 5 Chillin', Okay?!

Episode 8

Choices, Okay?!

Sun, Dec 12, 2021 28 mins

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, Molly spends an overwhelming day getting her parents' estate plan in order.

Episode 9

Out, Okay?!

Sun, Dec 19, 2021 28 mins

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.

Insecure Season 5 Out, Okay?!

Episode 10

Everything Gonna Be, Okay?!

Sun, Dec 26, 2021 41 mins

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.

Insecure Season 5 Everything Gonna Be, Okay?!
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