February 18, 2022

Illustrated by CJ Christy

It’s hard to say goodbye: The fifth and final season of HBO’s “Insecure” has concluded the journeys of main character Issa Dee, her best friend Molly Carter and the rest of the beloved South Los Angeles characters. 

The half-hour comedy-drama was created by and stars Issa Rae. It’s also loosely based on her 2011 web series “The Mis-Adventures of Awkward Black Girl.” The first season of “Insecure” premiered in October 2016. The final season, consisting of 10 episodes, began airing in October 2021. 

The final season primarily focuses on Issa (Issa Rae), Molly (Yvonne Orji) and Issa’s ex-boyfriend Lawrence Walker (Jay Ellis), moving forward in their careers and experiencing new adult milestones. At the beginning of this season, Issa finally creates her own community outreach program, The BLOCC, and is offered a speech at her alma mater, Stanford University. Molly advances at her law firm and re-adjusts to single life following a breakup from last season. Issa and Molly have tension within their friendship and are learning how to get back to trusting each other. Lastly, Lawrence prepares to move to San Francisco for a new job and welcomes new fatherhood amid a failed rekindled relationship with Issa. 

This season had many time jumps. The second episode jumps ahead one year later. The finale episode time-jumps by characters’ birthdays, which eventually leads to years. While I think this was a great idea, it felt very rushed for most of the time jumps to happen in the series finale. Instead of all the major conclusions bombarding viewers in the last episode, I think some elements could have been told or foreshadowed in earlier episodes of the season. There were so many ‘filler’ episodes this season that it left me having no idea how these characters’ stories could ever conclude. 

Despite these ‘filler’ episodes, some were memorable and had conversation-sparking scenes. Episode 3, titled “Pressure, Okay?!”, focused on the hassles of co-parenting between new parents, Lawrence and Condola (Christina Elmore), who are no longer in a relationship and live in different cities. Their conflicts with distance, Lawrence’s ability to travel in-and-out, and Condola’s hyper-independence ignited a heated — and realistic — argument between the two. It was one of the best acting scenes of the season.

Another great episode was Episode 5, titled “Surviving, Okay?!”, where Molly’s mother suddenly suffers from a stroke and is unconscious in the hospital. This episode showed the vulnerability of an adult facing the potential loss of their parent, as well the emotional growth of Molly’s character. Though she initially tried to push through with her own strength, she later admitted that she needed help and support during her family’s difficult time. She emotionally opened up more to her friends and even co-workers (one who eventually became her husband in the series finale). I do not believe Molly’s character would have done this in earlier seasons. Therefore, this episode proved to me that she had the best character development in the entire series. 

The last great filler episode was Episode 8, titled “Choices, Okay?!”, where Issa weighs the pros and cons of two potentially successful career paths, while also contemplating moving forward in her new relationship with boyfriend Nathan (Kendrick Sampson). She has two daydream sequences that show the future outcomes of either path she will take. Issa also reflects on her past choices, like leaving her old non-profit job and breaking up with Lawrence for the second time. Her past choices have a stifling effect on her making new ones. I appreciated this episode because the reflection on Issa’s past and future life may resonate with many other young adults currently contemplating the same.

Following the events of the penultimate episode, Nathan breaks up with Issa in the series finale and Issa undergoes the emotions of an average breakup. Later, while in the bathroom, she has a self-deprecating monologue with Mirror Issa — her comedic mirror reflection — and aptly says to herself, “I just want to fast-forward to the part of my life when everything is okay.” Ironically, the fast-forwards happen almost immediately after this scene. 

The series finale — titled “Everything Gonna Be, Okay?!” — jumps through time by the consecutive birthdays of Issa, Molly and their other two best friends, Kelli (Natasha Rothwell) and Tiffany (Amanda Seales). Their respective birthdays show Molly, Kelli and Tiffany moving on to build their families, getting married, moving out of state and having babies – meanwhile, Issa is discouraged and discredits herself when she is compared to them. Molly reminds her to look at how far she’s come and to be proud of her personal growth. Issa is now a successful businesswoman and community leader yet still feels ‘insecure’ about an old choice: Lawrence. After spending so much time being insecure in her decisions, the idea of herself, and worrying about her friends and peers’ expectations, she decides to let go and move forward. She and Lawrence reunite, get engaged, and Issa is finally content and ‘secure’ with her life.

Though some parts of the finale I did not like (i.e. Issa and Lawrence getting back together), it was satisfactory. Season Five was just ‘okay’ to me, compared to the previous seasons. However, the series overall is more than incredible; it’s dynamic.

“Insecure” is a great, introspective example of modern-day storytelling in American television. For example, the journey of Issa and Molly’s friendship showed how sisterhood can be a true love story. The show highlights the overlooked gems of South Los Angeles life and depicts Black characters in a way that seems rare to television — as humans. I definitely recommend “Insecure” for college students and millennial TV watchers — especially those who identify as Black or a person of color — as they may find it relatable to their unique, awkward coming-of-age experience. The victorious ups, the vulnerable downs and the awkwardness of Issa Dee’s world will truly be missed. 

Grade for the final season: B

Grade for the entire series: A+

Edited by Camila Fowler | cfowler@themaneater.com

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