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Managing editor & film and television critic with a Bachelor's of Arts in English Literature with a Writing Minor from the University of Guam. Currently in graduate school completing a Master's in English Literature.

Insecure reminds us what exactly is so insecure about itself. 

Issa Rae and Prentice Penny’s hit HBO comedy-drama series looks at different realities in juxtaposition with the main one. Its eighth episode is titled, “Choices, Okay?!” Executive story editor Eli Wilson Pelton serves as the writer of the teleplay, while Kevin Bray serves as the director.

In this review, I will be discussing the eighth episode of Insecure Season 5. There will be no spoilers present, as the title of this article suggests. Nonetheless, please read ahead at your own discretion.

Natasha Rothwell, Yvonne Orji, and Issa Rae in Insecure Season 5 Episode 8
Pictured from left to right: Kelli Prenny (Natasha Rothwell), Molly Carter (Yvone Orji), and Issa Dee (Issa Rae) in ‘Insecure’ Season 5 Episode 8: “Choices, Okay?!”. Photo credits to Merie Wallace/HBO.

Plot Synopsis

According to Warner Media, here is the synopsis of Insecure Season 5 Episode 8.

Issa finds herself at a crossroads in both her career and relationship. Molly spends an emotional day getting her parents’ will in order.

The Cast of This Week’s Insecure

As always, Issa Rae, Yvonne Orji, and Kendrick Sampson portray Issa Dee, Molly Carter, and Nathan Campbell, respectively. Natasha Rothwell and Courtney Taylor make appearances as Kelli Prenny and Issa’s assistant, Sequoia “Quoia”, respectively, while Jay Ellis and Leonard Robinson appear as Martin Lawrence Walker and Taurean Jackson.

Sharar Ali-Speakes, April Coffee, Amber Dancy, Gregory Freeman, Aisha Lomax, Tierra Peters, Kira Talise, and Roger J. Timber co-star. Dean Sharpe plays Keenan, a member of CrenShawn’s team, while Jahking Guillory plays Billy, a representative of Anthology Collective. Erick Mack Jr. plays Goop.

L. Scott Caldwell and Gregg Daniel guest star as Molly’s mother and father, Carol and David Carter. Meanwhile, Malcolm David Kelley and Richard Nevels guest star as Molly’s brothers, Jerome and Curtis Carter, respectively.

Kofi Siriboe plays CrenShawn. Jean Elie appears as Ahmal Dee, while Sahana Srinivasan and TJ Power return as Nadia Godal and her boss, Seth. Ruffin Prentiss appears as Thomas, Nathan’s cousin. Tyra Banks, Tyrone “Ty Dolla $ign” Griffin, and Elaine Welteroth also make guest appearances.

Natasha Rothwell in Insecure Season 5 Episode 8
Kelli Prenny (Natasha Rothwell) in ‘Insecure’ Season 5 Episode 8: “Choices, Okay?!”. Photo credits to Merie Wallace/HBO.

Discussion

Following last week’s episode, this week’s is cinematic and anxiety-inducing in all the great ways. “Choices, Okay?!” follows the series’ two female leads as they ponder on the choices that will define who they will be in the future. There was a joke or two on the comedy end that made me feel uncomfortable, but other than that, I had no issues.

Nena Erb returns as the editor, with Daniel Steely Esparza and Libya El-Amin joining Aneesa Nash as the assistant editors. They sure know how to fool the viewer!

Kimberly Berry, Elizabeth Burnett, and Crystal Haynes join Lindsay Rogers and Nichelle Young as the episode’s hairstylists. Reshena Burch joins Erika Williams, Jessica Davis, and Lisa Marie Evans in the set costumer team. Alex Kim, Naikea Cheri Ward, Reena Ray, and Evelyn Martinez join Diane Bunch as the costumers.

Much of the episode focuses on a recurring theme that we’ve seen on the show. This element of Insecure takes over, as if to show us what the future could be but maybe is not. It was dramatic in the Season 2 finale, but I think it has gotten old by this point. On the other hand, perhaps that’s just the writers playing with fans’ emotions. Nonetheless, the hair, the make-up, and the costumer teams did so well here that I need to commend them for their work.

Also, I love the music choices that Lehman put together, including some songs by Vince Staples and Kari Faux.

Issa Rae in Insecure Season 5 Episode 8
Issa Dee (Issa Rae) in ‘Insecure’ Season 5 Episode 8: “Choices, Okay?!”. Photo credits to Merie Wallace/HBO.

Performances and Character Developments

I need Rothwell and Elie to do another television series together. Whether as a spin-off or a show outside of the Insecure world, I just want to see them collaborate again. Rothwell deserves way more credit for her role in the series. Her role as Kelli Prenny in this week’s episode is small but is worthy of some merit.

The Carter family develop well, and there is something about Molly in particular that I like about her. Aside from her monologue towards the end, her relationship with Taurean is cute. I hope to see how this plays out in the next couple of weeks. With that said, I don’t know if I can say the same for Issa. There is something about her mind that haunts her, and I actually found myself terrified during the closing scene of the episode.

We finally see some development in Siriboe’s character, CrenShawn, as well as Robinson’s Taurean. There are many supporting and secondary characters in the series that I’d wish to see develop more. However, with just two episodes left in the series (I know, devastating!), I do not know how this will work.

Yvonne Orji in Insecure Season 5 Episode 8
Molly Carter (Yvonne Orji) in ‘Insecure’ Season 5 Episode 8: “Choices, Okay?!”. Photo credits to Merie Wallace/HBO.

Final Thoughts

I was not prepared for this episode. With 28-and-a-half minutes, you just need to take it for what it is. “Choices, Okay?!” reminds us that every single decision we make leads to excellence no matter which path we take. Even if we fail now, Insecure shows us that we will succeed in the long run. The way the writers convey this lesson to us could have been a little more realistic, but again, take it for what it is.

Insecure ends in two weeks, and I know many fans will cry or feel bittersweet for what is to come. Regardless, life lives on.

Insecure Season 5 is available to watch on HBO!

Have you seen this series yet? If so, what are your thoughts on it? Let us know! For more comedy and drama-related news and reviews visit and follow The Cinema Spot on FacebookTwitter, and Instagram!

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Managing editor & film and television critic with a Bachelor's of Arts in English Literature with a Writing Minor from the University of Guam. Currently in graduate school completing a Master's in English Literature.

John Daniel Tangalin

About John Daniel Tangalin

Managing editor & film and television critic with a Bachelor's of Arts in English Literature with a Writing Minor from the University of Guam. Currently in graduate school completing a Master's in English Literature.

View all posts by John Daniel Tangalin

4 Comments on “‘Insecure’ Season 5 Episode 8 Non-Spoiler Review – “Choices, Okay?!””

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