The Best Episodes of Insecure Season 5

Episode Rankings

1. #1 Fan Favorite
   

   1.9/10(316 votes)

   #1 - Reunited, Okay?!

   S5:E110/24/2021

   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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   Director:Melina Matsoukas

   Writer:Amy Aniobi
2. 

   1.8/10(276 votes)

   #2 - Growth, Okay?!

   S5:E210/31/2021

   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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   Director:Maurice Marable

   Writer:Phil Augusta Jackson
3. 

   2.1/10(285 votes)

   #3 - Pressure, Okay?!

   S5:E311/7/2021

   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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   Director:Ava Berkofsky

   Writer:Jason Lew
4. 

   1.9/10(241 votes)

   #4 - Faulty, Okay?!

   S5:E411/14/2021

   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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   Director:Maurice Marable

   Writer:Syreeta Singleton
5. 

   2.0/10(236 votes)

   #5 - Surviving, Okay?!

   S5:E511/21/2021

   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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   Director:Kerry Washington

   Writer:Laura Kittrell
6. 

   2.0/10(231 votes)

   #6 - Tired, Okay?!

   S5:E611/28/2021

   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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   Director:Natasha Rothwell

   Writer:Grace Edwards
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7. 

   2.0/10(233 votes)

   #7 - Chillin', Okay?!

   S5:E712/5/2021

   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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   Director:Amy Aniobi

   Writer:Fran Richter
8. 

   2.2/10(230 votes)

   #8 - Choices, Okay?!

   S5:E812/12/2021

   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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   Director:Kevin Bray

   Writer:Eli Wilson Pelton
9. 

   2.0/10(271 votes)

   #9 - Out, Okay?!

   S5:E912/19/2021

   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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   Director:Prentice Penny

   Writer:Prentice Penny
10. 

    2.1/10(384 votes)

    #10 - Everything Gonna Be, Okay?!

    S5:E1012/26/2021

    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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    Director:Prentice Penny

    Writer:Issa Rae