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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.

After over sixteen months, Insecure is back for its fifth and final season. Issa Rae and Prentice Penny’s Golden Globe and Emmy-nominated HBO comedy-drama series returns with its final storyline. (Frankly, I do not want it to end, but all good things must come to a conclusion, right?)

Its premiere episode is titled, “Reunited, Okay?!” Executive producer Amy Aniobi serves as the writer of the teleplay, while executive producer Melina Matsoukas serves as the director.

In this review, I will be discussing the first 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, Issa Rae, Amanda Seales, and Wade Allain-Marcus in Insecure Season 5 Episode 1
From left to right: Kelli Prenny (Natasha Rothwell), Molly Carter (Yvonne Orji), Issa Dee (Issa Rae), and married couple Tiffany (Amanda Seales) and Derek DuBois (Wade Allain-Marcus) in ‘Insecure’ Season 5 Episode 1: “Reunited, Okay?!”. Photo credits to Raymond Liu/HBO.

Plot Synopsis

According to Warner Media, here is the synopsis of Insecure Season 5 Episode 1.

At her ten-year college reunion, Issa’s self-doubt quickly surfaces, while Molly struggles to get out of her own head.

The Cast of This Week’s Insecure

As always, Issa Rae portrays Issa Dee and Yvonne Orji plays Molly Carter. Jay Ellis makes an appearance as Martin Lawrence Walker. Natasha Rothwell portrays Kelli Prenny, while Amanda Seales plays Tiffany DuBois.

Wade Allain-Marcus guest stars as Derek DuBois, Tiffany’s husband. Diallo Riddle portrays the panel moderator at Stanford University. Taja V. Simpson portrays Cheyenne, a former friend of the girls’ who likes to party.

Sahana Srinivasan plays Nadia Gopal, a panelist at the group’s Stanford University entrepreneurs event. David Beeler also appears as a panelist.

Writer/E.P. Amy Aniobi makes an appearance in the episode, while Raheem Williams plays Cheyenne’s partner in crime.

Latoya Blakely, Austin Grant, Michael J. Henderson, Armie Hicks Jr., Kristen Horde, Huneycut, Carolyn Jania, Alexander Jo, Abigail Killmeier, Clinton Lowe, Jeanae Melisa, Chinedu Unaka also star.

Issa Rae and Yvonne Orji in Insecure Season 5 Episode 1
From left to right: Issa Dee (Issa Rae) and Molly Carter (Yvonne Orji) in ‘Insecure’ Season 5 Episode 1: “Reunited, Okay?!”. Photo credits to Raymond Liu/HBO.

Discussion

First of all, let me say that this final season premiere for Insecure can get emotional… All the way to the end.

“Reunited, Okay?!” primarily takes place in a whole other part of California: San Francisco. It’s almost as if to foreshadow what we will be expecting in the stories of these beloved characters to come. From the moment Issa Dee steps foot in San Fran’, it will indeed feel incredibly new to fans. Big things are ahead for our central characters that are beyond after-school programs but still have their place in the Insecure world.

Aniobi’s writing is just splendid. There are several lines in the episode that, when coming out of the protagonists’ mouths, sound fitting. However, these lines also feel directed to the audience, especially now that we are in a post-Black Lives Matter 2020 protest period. While it’s been so long since the Season 4 finale, the characters remind us that they’re still around and they always will be. I can’t give all of the lines away, but one that resonated with me is this: “Are we gonna be okay?”

We have Shiona L. Turini’s costume design to thank for the characters’ outfits. Additionally, I must commend Shian Banks, Yvette Shelton, Nichelle Young, Felicia Leatherwood, Mary Daniels, Ashley Caldwell, Lindsay Rogers, and Deana Reed for their hair styling and artistry.

Also, it would not be Insecure without Raphael Saadiq’s music and the soundtrack curation. You might be familiar with some old-school artists (and I need to Shazam the song featured in the ending credits sequence) when you listen to them.

Performances and Character Developments

Rae continues to shine as the series’ protagonist and remains the “awkward Black girl” that she has been for quite some time. As teased by the Season 5 trailer, there are two scenes featured in the premiere in which she takes the spotlight. Let’s just say that she reflects a great deal on her life, and the way she delivers her performance is absolutely outstanding. It also allows the viewers themselves to get some retrospection on their journey over the past five years.

As always, I love the scenes that Rae’s Issa shares with Orji’s Molly. There are a couple of scenes that take the drama up by ten, the latter of which may give fans anxiety and fear. Regardless, when she’s with Issa, the character just makes every situation work.

Rothwell continues to make me laugh as Kelli Prenny. In a fashion similar to a character from Final Destination 5, Prenny serves as the comedic relief, a necessary component for the series. Without her, well… We can’t imagine what the show would be like. She gets a little deep towards the end of the episode, which is oftentimes unlike her. Although, I do appreciate this side of the character.

Seales and Allain-Marcus have good scenes together, especially in the small montage that involves a lovely voiceover. We need more of that. We need more of them!

Amanda Seales and Wade Allain-Marcus in Insecure Season 5 Episode 1
Tiffany (Amanda Seales) and Derek DuBois (Wade Allain-Marcus) in ‘Insecure’ Season 5 Episode 1: “Reunited, Okay?!”. Photo credits to Glen Wilson/HBO.

Final Thoughts

Fans of Rae and Penny’s Insecure will love this final season premiere. It builds upon conclusions that are still a time away. Like certain episodes from the past four seasons, it will have you laughing, it will have you crying. In the end, it provides us with an answer to one question in particular.

Yes, we will be okay.

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