‘Insecure’ Season 5 Episode 7 Non-Spoiler Review – “Chillin’, Okay?!”

“This is the power of the game … and the only thing left to do is to let it happen.”

Issa Rae and Prentice Penny’s hit HBO comedy-drama series Insecure lets loose on what its characters are keeping inside. Its seventh episode is titled, “Chillin’, Okay?!” Series co-producer Fran Richter serves as the writer of the teleplay, while executive producer Amy Aniobi serves as the director.

In this review, I will be discussing the seventh 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.

Plot Synopsis

According to Warner Media, here is the synopsis of Insecure Season 5 Episode 7.

A much-needed girls’ night puts things into perspective for Issa and her crew.

The Cast of This Week’s Insecure

As always, Issa Rae portrays Issa Dee, while Yvonne Orji plays Molly Carter. Natasha Rothwell and Amanda Seales return as their respective characters, Kelli Prenny and Tiffany DuBois.

Kendrick Sampson appears as Nathan Campbell, while Jay Ellis returns as Martin Lawrence Walker. Christina Elmore guest stars as Condola Hayes, while Elle Lorraine makes a guest appearance as Trina, Issa’s neighbor.

The Crew

Some faces taking up new positions for the new episode are as follows.

Daysha Broadway joins the final season as the episode’s editor, while Lilit Aloyan joins Aneesa Nash as the assistant editor.

Yvette Shelton serves as the department head hair, while Shian Banks takes control as the key hair stylist. Michelle Bear and Yvettra H. Grantham join Lauren Guzman, Mark Starr, and Alyssa Hudson as the make-up artists, while Nichelle Young joins Lindsay Rogers and Deana Reed as the hairstylists.

Diane Bunch serves as the primary costumer for the episode, while Annapurna Kreaden (Euphoria), Halle Schirmer, and Blake Turner serve as costume production assistants.

Erick Garibay serves as the supervising prop master, while Meaghun Crookston-Valdez serves as the property master. Cody Shields serves as the assistant prop master, while Cara Cirrincione is the assistant on props. Nina Acuna, Eleanor Jenkins, Rraine Hanson (Pen15), and Joanna Way serve as the props production assistants.

Discussion

This upcoming episode of Insecure passes the Bechdel Test every now and then. Its title means more than chilling around and hanging out. Issa has her friends get together and try to decompress. They don’t let their current circumstances ruin their night, resulting in what Kelli refers to as a “Jumanji ass game”. In fact, that’s just how it feels.

The truths that manifest are—for the most part—reflections of how far the characters have come. It returns to something Kelli says during her podcast at the end of the final season premiere:

If you knew the end was coming, how would you make the most of your time left? What legacy would you want to leave behind? How would you want to be remembered? Is there anything you would change?

This is the recurring theme for the season, as well as what happens when something unexpected comes to the surface.

Turini and the costumers, along with the hair and make-up artists, do a great job at making appearances worthwhile, even if they are transient. Not only that, but Saadiq and Lehman put together a great score and soundtrack, including a couple of old-school songs from the mid-to-late 2000s. By the end, the entire teaches us that where you need to go and whom you desire to be is not that far from reach.

Performances and Character Developments

Kelli and Tiffany’s revelations about themselves start off hilarious but eventually bring in some gravity. The series prepares to conclude the characters’ respective stories, including a way to give Seales an ending to Tiffany DuBois.

This Insecure episode calls upon some of the current and previous men in Issa’s and Molly’s lives. Molly is unsure of what to do about her workplace relationship, which looks like it could be going somewhere, that is if she plays her cards right. Meanwhile, Issa discusses what she’s discovered and where she’s at in the series. I have no doubt she’ll progress from here in the next three episodes. However, I fear that if she Hannah Horvath’s this at the last moment, then we won’t see her aspirations meet full fruition. (I doubt this will happen though since Rae herself has discussed plans to not Game of Thrones the series finale.) This begins with a resolution on Nathan’s part, which provides what was hoped for two episodes ago.

On the Other Hand…

Lawrence and Condola’s relationship begins to head in a good direction, resuming their little story arc from a few episodes prior. Although, in juxtaposition with the girls’ Jumanji journey, this couple goes through something darker in tone. It’s a rather serious matter as if the series is aware of the social media scrutiny surrounding Condola. Elmore’s delivery of a line and Ellis’s performance as reacting to it is spot on, and I do believe Lawrence has what it takes to become a rather remarkable father.

By this point, we should know that she is not the bad guy for the trajectory the series has taken. One character asserts something that we as human beings need to ponder and that can apply to everything about the show and in life so far:

Sometimes it’s not about making the smart choice. It doesn’t have to make sense to you, and it doesn’t have to be the smart choice to be the right choice.

Final Thoughts

At a runtime of twenty-eight and a half minutes, there could have been just another two or three more minutes to focus on Kelli and/or Tiffany. Other than that, the writing can get pretty poignant about the potential possibilities of the past. Perhaps that’s why the passion is potent. No matter what happens, you are going to need people who will help you get to the end. Together, you will never be totally stranded in life; as Tyler, the Creator’s recent album says, “Call me if you get lost”!

Overall, what all looks perfect on the outside is not so within. “Chillin’, Okay?!” takes a look at the human conditions of its characters and psychoanalyzes the various drives that get them going.

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 Facebook, Twitter, and Instagram!