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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.

“Here’s to love, life, and great friendships”. Following last week’s episode, Issa Rae and Prentice Penny’s hit HBO comedy-drama series Insecure nears its conclusion. Season 5’s ninth episode is titled, “Out, Okay?!” Series co-showrunner/ executive producer Prentice Penny serves as both the writer and the director.

In this review, I will be discussing the penultimate episode of Insecure. There will be no spoilers present, as the title of this article suggests. Nonetheless, please read ahead at your own discretion to avoid any potential reveals.

Jay Ellis in Insecure Season 5 Episode 9
Martin Lawrence Walker (Jay Ellis) in ‘Insecure’ Season 5 Episode 9: “Out, Okay?!”. Photo credits to Merie Wallace/HBO.

Plot Synopsis

According to Warner Media, here is the synopsis of Insecure Season 5 Episode 9.

Issa navigates unresolved feelings when tensions escalate at a friend’s going away party. Molly lets loose with her new man.

The Cast of This Week’s Insecure

As always, Issa Rae and Yvonne Orji portray Issa Dee and Molly Carter, respectively. Natasha Rothwell and Amanda Seales play their respective friends, Kelli Prenny and Tiffany DuBois. Jay Ellis, Kendrick Sampson, and Leonard Robinson star as Martin Lawrence Walker, Nathan Campbell, and Taurean Jackson, respectively.

Jessica Combs, Tara Renee Cook, and Matt Pascua also star in the episode. Prentice Penny, story editor Mike Gauyo, and writers’ room assistant Chris Sanford also make appearances.

Wade Allain-Marcus, Neil Brown Jr., and Christina Elmore guest star as Derek DuBois, Chad Kerr, and Condola Hayes, respectively. Jean Elie appears as Ahmal Dee, Issa’s brother, while Sarunas J. Jackson plays Alejandro “Dro” Peña, Molly’s former flame.

Nikiva Dionne and Kelsey Scott appear as Stacy Sutton and Felicia, Molly and Taurean’s respective colleagues at the Hayward firm. Curtis Hamilton appears as Aric, Nathan’s co-worker at the barbershop.

Wade Allain-Marcus in Insecure Season 5 Episode 9
Derek DuBois (Wade Allain-Marcus) in ‘Insecure’ Season 5 Episode 9: “Out, Okay?!”. Photo credits to Merie Wallace/HBO.

Discussion

Ava Berkofsky returns as the cinematographer. Daysha Broadway returns as the editor, while Lilit Aloyan joins Anessa Nash in assistant editing. Ashley Caldwell returns as Rothwell’s hairstylist. Deana Reed joins Lindsay Rogers and Nichelle Young in the hairstyling department, while Eric Gonzalez joins Erik Taylor as barbers. Shelli Bradley, Kristina Elaine Taylor, Lyndrea Price, and Taylor Bakkenson join Diane Bunch and Alex Kim as the costumers.

Much of the episode is owed to its musical curation, principal photography, and overall editing. In my opinion, however, the highlights are Turini’s costume design, the costuming department, Burton and Cox’s set designing, and Haley’s set decorating. As the above synopsis implies, the episode takes place at a party for the DuBois family. This means Tiffany and Derek’s friends are the party attendees, which means… It will not end well at all.

I am curious as to how the teleplay screenwriting translated to the small screen. The execution of the plot as well as the delivery of lines of the dialogue felt spot on. Things appear to be fine at first, that is until we see Lawrence, Nathan, Taurean, and Dro, along with Chad, Derek, and Ahmal amongst other men gathered together to the side during one point of the party. From here, matters become nerve-racking and you are left wondering how the entire series will be wrapped up in its finale episode alone. What exactly is the endgame here?

There’s also an interesting scene focused on the main female characters of the series. This involves a comedic delivery from Orji, a hilarious reaction from Issa, and the arrival of an outside party. It’s not as bad as the previously described scene, but I still enjoyed it nonetheless.

Performances and Character Developments

Orji and Robinson’s performances go sky high as their characters, Molly and Taurean, flourish and make their relationship a little more public. Their dynamic is hands down my favorite part about the episode. We would have not believed it if we were told in Seasons 3 and 4, but Taurean’s really grown on us in the few episodes of the final season that he’s been in. The scenes they share are lovely, especially one in which they get down with some party food. (Talk about food porn…) It’s one of the better moments of the episode, and I’m sure fans will love it the most as much as I have.

As for other characters, I found myself disappointed. There is something suspicious about Nathan that I don’t like, and Lawrence has devolved from the character fans have grown to love. I fear for them both, and I have an eerie feeling that the series finale will result in someone’s death, or at least, someone getting hurt badly. Imagine watching them develop over the course of the season, only for that to be tarnished. That is how I felt by the end of the episode.

Aside from Molly and Taurean, Issa also presents a solution to an issue. She suggests a way for her and her girlfriends to reunite after the DuBois family leaves for Denver. This could maybe, just maybe, tease a possible reunion special for the show in the near future, but who knows?

I also liked the inclusion of Jackson’s Dro in this episode. He’s changed since the last time fans have seen him, which feels like forever ago. As he claims, “Shit happens”.

Yvonne Orji in Insecure Season 5 Episode 9
Molly Carter (Yvonne Orji) in ‘Insecure’ Season 5 Episode 9: “Out, Okay?!”. Photo credits to Merie Wallace/HBO.

Final Thoughts

“Out, Okay?!” takes note of the “awkward energy” shared between the series’ characters. Not all of them return for this episode, but those that do demonstrate something wrong that is still going on about themselves. These are the characters whose issues need to be addressed. What went wrong, and how can these problems be mended? That’s where the writing tends to be flawed; almost nobody has been fixed by now. What started with Issa’s insecurity at the beginning of the series has spread to the others, and I would be a little remiss if I said it’s not infectious.

Everything is messy, but I do hope the series finale will wrap things up by Christmastime. If not, then it might just continue to eat away at our minds. The roughest part was examining the differences in characters’ backgrounds. You would think that they would get along with their similarities, but that is not the case. What’s worse is it doesn’t look like it will be possible to come back from that.

Insecure Season 5 is available to watch on HBO, and stay tuned for next week’s series finale!

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

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