Insecure (Season 5)

She's trying hard AF.

Follows the awkward experiences and racy tribulations of a modern-day African-American woman.

  • Poster for Reunited, Okay?!

    Reunited, Okay?! (Episode 1) 1.9

    Writer: Amy Aniobi

    Air date: 2021-10-24

    Runtime: 32 min

    Overview: 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.

  • Poster for Growth, Okay?!

    Growth, Okay?! (Episode 2) 1.8

    Writer: Phil Augusta Jackson

    Air date: 2021-10-31

    Runtime: 29 min

    Overview: 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.

  • Poster for Pressure, Okay?!

    Pressure, Okay?! (Episode 3) 2.1

    Writer: Jason Lew

    Air date: 2021-11-07

    Runtime: 28 min

    Overview: 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.

  • Poster for Faulty, Okay?!

    Faulty, Okay?! (Episode 4) 1.9

    Writer: Syreeta Singleton

    Air date: 2021-11-14

    Runtime: 28 min

    Overview: 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.

  • Poster for Surviving, Okay?!

    Surviving, Okay?! (Episode 5) 2.0

    Writer: Laura Kittrell

    Air date: 2021-11-21

    Runtime: 25 min

    Overview: 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.

  • Poster for Tired, Okay?!

    Tired, Okay?! (Episode 6) 2.0

    Writer: Grace Edwards

    Air date: 2021-11-28

    Runtime: 27 min

    Overview: 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.

  • Poster for Chillin', Okay?!

    Chillin', Okay?! (Episode 7) 2.0

    Writer: Fran Richter

    Air date: 2021-12-05

    Runtime: 29 min

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

  • Poster for Choices, Okay?!

    Choices, Okay?! (Episode 8) 2.2

    Writer: Eli Wilson Pelton

    Air date: 2021-12-12

    Runtime: 28 min

    Overview: 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.

  • Poster for Out, Okay?!

    Out, Okay?! (Episode 9) 2.0

    Writer: Prentice Penny

    Air date: 2021-12-19

    Runtime: 29 min

    Overview: 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.

  • Poster for Everything Gonna Be, Okay?!

    Everything Gonna Be, Okay?! (Episode 10) 2.1

    Writer: Issa Rae

    Air date: 2021-12-26

    Runtime: 41 min

    Overview: 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.

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