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The Best Episodes of Insecure Season 5

Every episode of Insecure Season 5 ranked from best to worst. Discover the Best Episodes of Insecure Season 5!

Binge this in 4h 56m•Peaking at 8.3/10

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

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Episode Rankings

  1. #1 Fan Favorite
    Insecure Season 5 Episode 9 - Out, Okay?!
    8.3/10(277 votes)

    S5:E9

    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.

    Director:Prentice Penny
    Writer:Prentice Penny

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  2. Insecure Season 5 Episode 10 - Everything Gonna Be, Okay?!
    8.3/10(392 votes)

    S5:E10

    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.

    Director:Prentice Penny
    Writer:Issa Rae

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  3. Insecure Season 5 Episode 1 - Reunited, Okay?!
    7.8/10(321 votes)

    S5:E1

    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.

    Director:Melina Matsoukas
    Writer:Amy Aniobi

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  4. Insecure Season 5 Episode 3 - Pressure, Okay?!
    7.8/10(288 votes)

    S5:E3

    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.

    Director:Ava Berkofsky
    Writer:Jason Lew

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  5. Insecure Season 5 Episode 7 - Chillin', Okay?!
    7.8/10(238 votes)

    S5:E7

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

    Director:Amy Aniobi
    Writer:Fran Richter

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  6. Insecure Season 5 Episode 8 - Choices, Okay?!
    7.7/10(235 votes)

    S5:E8

    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.

    Director:Kevin Bray
    Writer:Eli Wilson Pelton

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  7. Insecure Season 5 Episode 5 - Surviving, Okay?!
    7.6/10(239 votes)

    S5:E5

    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.

    Director:Kerry Washington
    Writer:Laura Kittrell

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  8. Insecure Season 5 Episode 6 - Tired, Okay?!
    7.5/10(234 votes)

    S5:E6

    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.

    Director:Natasha Rothwell
    Writer:Grace Edwards

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  9. Insecure Season 5 Episode 2 - Growth, Okay?!
    7.3/10(280 votes)

    S5:E2

    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.

    Director:Maurice Marable
    Writer:Phil Augusta Jackson

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  10. Insecure Season 5 Episode 4 - Faulty, Okay?!
    7.3/10(244 votes)

    S5:E4

    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.

    Director:Maurice Marable
    Writer:Syreeta Singleton

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Season 5 Ratings Summary

"Out, Okay?!" is the best rated episode of "Insecure" season 5. It scored 8.3/10 based on 277 votes. Directed by Prentice Penny and written by Prentice Penny, it aired on 12/19/2021. This episode is rated 0.0 points higher than the second-best, "Everything Gonna Be, Okay?!".