“Insecure” Recap: Season 5, Ep. #6 – “Tired, Okay?”

First of all, can you believe that we’ve already reached 6 episodes and 5 weeks of watching and discussing our favorite show, “Insecure”…? It’s crazy how the time has flown while watching and consuming this amazing black show. It’s just another testament to what we’ve been missing in our TV viewing experience. Hopefully, “Insecure” isn’t the end of the kind of experience we’re owed. 

And second of all, I might have a few I-told-you-so’s on deck, because Episode #6 of “Insecure”, Tired, Okay?, pretty much cemented many of the things we discussed in our recap of episode #5 of “Insecure”.

On to the recap! 

The show starts off where we left off, with Issa walking past Condola and Lawrence in the hospital. At the start, she approaches the couple, appears to give civility an attempt, and ends up holding their baby. But out of nowhere, Issa ends up shooting the baby like a basketball across the room, kicking Condola into a pile of clothes, and walking away snickering after yelling at Lawrence. But as Biggie said, it was all a dream. 

Upon waking up from her dream, she immediately checks Lawrence out on Instagram, only to see that he has now moved back to Los Angeles. Issa is bothered by this but moves on with her day.  


Issa is back to the grind with The Blocc, but as she’s pitching what appears to be an upcoming group of artists, the group sours on her once they seemingly connect her with the ire of Crenshawn, who in previous episodes has been spewing all types of hate her way over social media. In an effort to ease the tensions and stop Crenshawn from affecting her business, Issa goes to Crenshawn, awkwardly with brownies, and tries to make amends. But Crenshawn isn’t having it, claiming that he and Issa had shared all types of visionary conversations about doing so much for the neighborhood, only for her to, as he sees it, turn her back on his creative vision and not dilute it for Corporate America. Issa clearly feels different, but her decision and/or inability to offer up the reasoning for her decision to not go down with the ship suggests that maybe she does feel like she made the wrong decision. Personally, I think she did what she had to do to make progress, just like many black people have done throughout the last century (and beyond) by taking jobs that were beneath them so that those who came after them wouldn’t have to. But she never makes that argument or any real argument. Meanwhile, Crenshawn shows her his new line based on Issa. It’s called “Integrity”. 

Molly Doing It All 

Last we saw, Molly was trying to control everything at the hospital, while she waited for her mother to come out of a coma. Now, she is squarely in the middle of a work retreat, responsible for a huge presentation, but still extremely worried about her mom’s health. We first see her talking with Issa over Facetime as Issa is at the hospital attempting to do all of the things Molly would like to be doing, like feeding her family, keeping everybody up to date, and monitoring her mother’s progress. 

Molly’s time at the work retreat; however, is increasingly compromised by her being worried about what’s going on at work. After finding out that despite her colleagues’ bad first impressions of her, they now love her, she lets loose for one night and wakes up hungover with a strange man’s watch in her bed. Upon arriving at breakfast with those same colleagues, who appear a lot less hungover than her, they play a video of her getting down and confiscating Taurean’s watch. Later on, Molly messes up a presentation because she’s worried a call she is avoiding while she’s talking to her firm’s partners is about her mom. Taurean saves the presentation, causing Molly to eventually confide in him about what’s going on with her mom. They end up embracing each other in an awkward hug, which no doubt created a ton of sexual tension between the two. 

Issa’s Love Life

Still hung up on the fact that Nathan has said “I love you” back to her, Issa tries to get Nathan to say while riding him during sex. The boy still won’t do it. But after a kerfuffle at the barbershop in which Nathan gets called bipolar by a late and disgruntled co-worker, Nathan comes home hot and tells Issa that he’s not sure LA is the right place for him anymore. Annoyed by Nathan’s inability to acknowledge her “I love you”, she calls him out for his lack of commitment. Nathan suggests that Issa’s up-and-down feelings about him are the reason he can’t really commit to her, but admittedly, that seems like more of an excuse than a reason. While this is something that certainly something that the two could recover from, based on the way Nathan is responding to a simple argument at work, it would seem like he’s not going to be able to give Issa the love she needs–especially if there’s someone out there who wants to. 

Speaking of which, the thought of Lawrence returning to LA seems to be on Issa’s mind. While getting food, she has another dream, this time with Condola enacting her revenge, bragging to Issa that Lawrence came back for her, is a much better man with a 2-inch longer penis, and makes 1-billion dollars per month. Condola ends the conversation with a kick to Issa’s head, returning the favor from the dream from earlier before. 

Obviously, it’s no coincidence that Issa is having these thoughts about Lawrence. These two paths are going to cross again during the final four episodes of this series. The question remains, will she choose Lawrence, Nathan, herself (as the overthinking crowd likes to propose), or my new darkhorse, Crenshawn, as her future lover. 

The case for Nathan is that he’s a grown man, with grown tendencies, and while he certainly has mental health problems he deals with, seems to be the respectable guy that treats her with respect. Of course, he now seems to have commitment issues, and the last thing Issa needs is someone who can’t be there for her–at all times. 

The case for Lawrence is obvious. They have a history. And while that by itself is not enough, the truth is that they really only broke up because of Issa’s cheating. Right before they broke up, Issa was rushing back home to see this man and try to get her to forgive her for cheating on him. At the time, Lawrence had come out of his funk, got a new job, and felt like a new man. Had Issa been honest with, there’s a chance she would have been around to be with the guy Lawrence ultimately became. Yet, the case against Lawrence is that they have a history. Lawrence isn’t perfect, was a bit of a fuckboy during his single days, and has self-confidence issues of his own. But any man that gets cheated on, experiences single life, climbs the corporate ladder, and wants to come back to his old girlfriend is probably someone worth having in your life. 

As for Crenshawn, from the very first episode, I thought there was a bit of sexual tension between Issa and this guy. I didn’t have much to go off of except for an early working chemistry between the two. However, in this episode of “Insecure”, I feel like the animosity between them was from a well-meaning place, and then they brought up the long talks they had about the neighborhood, and I’m now convinced that they just might be exact opposites with a common goal. Watch out for this one–I could see it happening. 

And then, of course, there’s this crazy idea that Issa might just choose herself in the end. Obviously, there’s nothing wrong with that, but that’s just stupid talk. She should definitely choose herself, but that shouldn’t require, as the users of the saying suggest, that she not find love. If that’s what she wants, then choosing love, and choosing to sacrifice some aspects of your everyday life for the pursuit of that love, is a very respectable choice. Would it be great if Issa could be as happy as anyone by choosing to be single? Sure. It would be great for us all. But unfortunately, companionship and loneliness are real things, and having a loving partner is a perfectly natural and healthy thing to pursue–so long as you’re happy with yourself. And if you really think about this season of “Insecure” thus far, we’ve been given little reason to think Issa isn’t at a very happy place in her life. 

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