REVIEW: Insecure Season 4 is High-key Phenomenal and Ends with a Major Bombshell

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Insecure, is the the hit millennial comedy-drama television series on HBO created by Issa Rae and Larry Wilmore. Partially based on Rae’s renowned web series Awkward Black Girl, Insecure unpacks the story of the Black female experience from the perspective of two female protagonists, Issa (Issa Rae) and Molly (Yvonne Orji) who have been best friends since college.

Both women are in their late 20s, as they try to navigate career and relationship experiences while living in Los Angeles, California. The two share a close bond, and throughout the show, they deal with internal struggles within themselves, their friendship, and the African American community.

Due to Rae’s other projects and commitments season, four’s premiere was delayed for nearly two years. Leaving fans eager to see what was to come next for the two besties. This season takes place a few weeks after the season three finale. Issa is months away from planning her Block Party with help of her new friend Condola (Christina Elmore), an event that is meant to be a celebration of Black culture and local Black-owned businesses in the Inglewood community.

Meanwhile, Molly is figuring out her budding romance with  Andrew (Alexander Hodge) and what level of commitment they are at and whether or not this relationship will end in disappointment like her other ones. However, a divide grows between the besties as Issa and Molly’s jabs and shots at one another quickly go from friendly to toxic, as they each are judgmental of the other’s choices and actions.

In the first few moments of this new season of Insecure we learn that Issa and Molly’s friendship is not what it used to be. “Honestly … I don’t fuck with Molly anymore,” Issa says to the unknown caller on the other end of her phone call. From there the season takes the audience through five flashback episodes showing how the divide in their friendship and hostility towards one another grew over the course of a few months that lead up to their blow-up at Issa’s big event.

From the beginning Insecure, has been a show that explores the complexities of Blackness. That’s one of the reasons I love it so much. It is not a show that is meant to be the be-all-end-all representation for Black experience and culture. While it does a phenomenal job of capturing nuances that are specific and relatable to Black audiences, but it doesn’t try to be everything to everyone who is Black.

For a half-hour show, Insecure, does a great job of pacing and building the story consistently in each episode. It is a show that tells the story about regular people who are trying to navigate the complexities of their lives as Black people. Careers and dating, to relationships and friendships, are all things a part of day to day lives that Insecure explores it in ways that makes it relatable and genuine.

Something that I was very impressed with this season was Issa’s growth as she stepped into the career that she felt fulfilled in. Last season, Issa came to the realization that she couldn’t work at We Got Y’all a non-profit organization that specialized in after-school study programs. Regardless of not having another job opportunity lined up, she makes the bold decision to leave the only job she’s had since graduating college.

So when season four begins it was great to see that Issa was following through with her passion project of throwing a block party in Inglewood that showcased Black culture, music, and local businesses. And not only was she following through with it but it seemed like she had found this new sense of confidence and self-worth in the work she was doing.

In my opinion, this is something many millennials of today can relate to on some level, I know I can. You graduate from college and take the first job you can get so you can start paying bills and student loans. However, as time goes on you don’t find enjoyment or fulfillment in the work you do. To me, watching Issa find her fulfillment and a new career in her passion project is a good reminder that it is never to late to go into the work you want do. It won’t be easy, but it may be worth it in the end.

Insecure Issa Tiffany

Throughout the season the show lightly touches on topics and issues such as gentrification, prejudice in healthcare, and mental health. While I enjoyed these topics being highlighted the show does not always explore them on a deeper level. Thankfully this season it does take a deeper look at mental health. specifically when it came to Issa and Molly’s mutual friend, Tiffany.

After Tiffany (Amanda Seales) gives birth to her first child it is clear that she is dealing with postpartum depression. While it is not verbally confirmed that she has postpartum depression  we are shown throughout the season that something was up with Tiffany after she gave birth.  She seemed detached and less involved with her newborn baby. It wasn’t until the season finale, when she breaks down after her husband and friends find her in a hotel that she ran away to because she just didn’t know what else to do.

Another example of mental health being explored more this season that I appreciated was the insight into Nathan’s (Kendrick Sampson) personal struggles with mental health. Nathan was a previous flame of Issa’s from last season that ghosted her towards the end of season three . He returns this season and finally explained to Issa the reason he ghosted. It was because he found out he has a bipolar disorder. While I don’t feel his explanation completely wipes away the hurt that Issa felt, but I do think that him sharing his diagnosis is the start of their friendship growing in the right direction.

One of my biggest hopes for next season is that we see both of Tiffany and Nathan’s journeys with mental health continue. I think it would be worthwhile for the show to continue to acknowledge these character’s as they live and manage their respective mental illnesses. Another thing that I liked about this season that it really hits home the point that relationships, whether they are platonic or romantic, take work. A great example of this is Molly and Andrew’s relationship. It seemed like Molly had finally found the one when she and Andrew started dating and then made their relationship official. He seemed to understand her needs, was patient with her demanding work schedule, and more.

However, just because everything seemed fine didn’t mean it was fine. I’d be lying if I said I didn’t see Andrew breaking up with Molly coming. This season we saw countless times how Andrew gives in their relationship while Molly takes and doesn’t reciprocate the same to him. Every time that Andrew mentions something that bothers him, Molly doesn’t give him the same energy back Everything is on her schedule and on her terms. Which would get old fast for anyone, but Andrew was a saint for as long as he put up with it.

Molly on the other hand felt like they could work through their problems together and wasn’t willing to give up on them after all of the time they put into together. However, when Andrew asked her “What are you even fighting for?” and she didn’t have an answer to his question which in a way was her answer. She didn’t know why she wanted to fight for their relationships besides the fact that it was the longest relationship that she had ever had. Sadly, putting in time in a relationship isn’t enough, you also have to put in the work.

I truly feel for Molly and her situation with Andrew but in a way, she brought this on herself. She knows she wants to be in a relationship, but I don’t think she really knows or realizes all the work that goes into cultivating and maintaining a healthy relationship. Hopefully, she will take some time after this break up to self-reflect and figure what it is that she really wants and if she is willing to put the work in for it.

Insecure Molly and Andrew

Just like romantic relationships, friendships also take work. The main plot of this season focused on Issa and Molly’s friendship or rather the lack there of it.”You were coming for me!” Molly defensively says to Issa after one of her sharp and passive-aggressive critiques about Molly’s dating life. “And I feel like you’ve been coming for me. What’s going on?” Issa responds.

When Issa finds out that Condola is her ex’s new girlfriend, Molly is judgmental and calls Issa messy for continuing a cordial friendship with Condola while she engages in a cordial relationship with Lawrence. At the same time, Issa loses patience with Molly’s negativity and judgmental attitude. While Molly grew weary of Issa’s selfishness and not taking her relationship with Andrew seriously.

Initially, as a long-time fan of this show, I was surprised that Issa and Molly’s friendship had gotten to the point where it was falling apart before my eyes. I’ve always felt that their friendship is one of the cornerstones that made the series so good. However, just because their friendship was taking a wrong turn didn’t mean the quality of the show suffered. In fact, I think this new phase of their friendship pushes not only the story’s limits but also the actors’ limits in a way that helps contribute to Insecure delivering another quality season.

It is easier said than done, to believe that all Issa and Molly needed to do was have a good heart to heart talk in order to make bygones be bygones. But it is clear to see that the issues in their friendship didn’t just suddenly appear out of nowhere this season. Their issues and hostility towards one another have been building up for a long time, it was just that this season is where they reached their limits with one another.

Thankfully the season closes out with them meeting up at their favorite Ethiopian restaurant, a callback to season one, to finally have the talk they needed to mend things between them. I was let down that the audience doesn’t get to hear any parts of that conversation between the two of them. Especially since Insecure has written some amazing heart to heart conversation scenes. However, my biggest hope for next season is that this conversation is the first step that leads Issa and Molly to put more effort into communicating and actively working on their friendship together. I find it hard to believe that one conversation will fix all of the underlying issues in their friendship, but I do believe it is the step in the right direction for the duo.

Lastly, this season of Insecure does not go out with dropping some major bombshells. One in particular directly impacts Issa and her newly rekindled relationship with her former ex, Lawrence. We learn directly from Lawrence that Condola, his most recent ex, and a former work acquaintance of Issa’s is pregnant with his baby and she plans to keep the baby. Even though it happened before he and Issa got back together and before he got the new job in San Francisco. The news still hits Issa in the chest like a sack of bricks. It’s a lot for her handle and process all at once. Just when it seems like things with her and Lawrence were finally getting a fresh start together. Now with this news, the path of their future doesn’t seem so clear anymore and is paved with challenges ahead for next season.

Overall, season four of Insecure, was phenomenal! This season truly hits the message about relationships and friendships. While also touching on other many great topics. I was extremely pleased that this season expounds on characters dealing with different types of mental health. The season is also paired with a stellar soundtrack that consistently compliments every episode. While Insecure’s season four finale doesn’t quite give the resolution I was expecting, but it does on a note that makes me eager to see what’s to come in the next season.

Insecure, Season 4


Overall, season four of Insecure, was phenomenal! This season truly hits the message about relationships and friendships. While also touching on other many great topics. I was extremely please that this season  expounds on characters dealing with different types of mental health. The season is also paired with with a stellar soundtrack consistently compliments every episode. The finale doesn’t quite give the resolution I was expecting, but it does on a note that makes me eager to see what’s to come in the next season.

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