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The “Insecure” Fast Forward: Issa and Molly

When we ended episode 1 of this last season of “Insecure”, Molly and Issa started an awkward new phase in their friendship in which they were seemingly re-figuring out how to be around one another. The episode ended with them being robbed at gunpoint, a traumatic event that seemingly pushed them right out of that awkward phase and back to a place of realization where they are each other’s best friend and there’s no one they’d rather be in hard times with than one another. 

At the outset of episode #2, “Insecure” skips past any depiction of what that armed robbery may have immediately led to, by fast-forwarding the time by 1 year after showing us a montage of Issa and Molly. In the montage, we see them at work and thriving, and poignantly, Molly has a new natural hairstyle. 

At the outset of the new year, one of the early scenes has Molly and Issa hanging out, just as they were depicted constantly together in the montage. Now in real-time, Molly is getting sleepy as they watch TV, a huge departure from “Insecure” seasons past when the two were usually hung up over whatever show was at the pinnacle of the fictional world’s cultural zeitgeist. Now, the showrunner for “Insecure”, Prentice Penny, has explained that the typical “show within a show” dynamic that we’ve come to love every season of “Insecure” was cut due to Covid budgeting overflows. However, to me, it’s actually quite interesting that after a year of being engrossed in one another and their respective jobs, these two, mid-thirty, busy, black women find themselves too tired to partake in some of the frivolous things they used to. Call me an ageist if you will, but as a mid-thirties person myself, staying up and watching TV all night after a full, mentally draining day of work is not the thing you do. And with these folks seemingly, as portrayed in the montage, so engrossed in working on themselves and their careers, it’s not surprising that they tap out on some of the more social aspects of life–something Issa does later in the episode, which we’ll get to shortly! 

The Blocc

Speaking of work, things are going really well for Issa. She has a full-time employee on her staff who seemingly works out of Issa’s apartment and occasionally prepares her breakfast in a bag. We discovered that shortly after Issa celebrated crossing the 10k follower mark on Instagram, for which I think it’s worth noting the more millennial edge to “Insecure” (which is fine by me), because all of the cool kids are on TikTok now! 

Throughout this episode of “Insecure”, I actually become quite confused about what The Blocc is. In her talks with Nathan (yes, he’s back), Molly, Issa’s assistant (?), and even with Issa herself, there are the occasional references to events she’s thrown over the past year, as well as future things that she’s working on, but to me, it’s never 100% clear what The Blocc is doing–until maybe the absolute very end. Before that though, when she’s giving a major presentation to a group of staunch corporate-looking individuals, I’m not really sure what she’s pitching, I just know the two corporate guys aren’t feeling it, and they ask her to tone down her idea. Who they worked for, or what exactly she was pitching, seemed very unclear a the moment. 

What we do know is that Issa doesn’t want to tone her idea down, so in an attempt to go over the heads of the guys who gave her the unfavorable response, she tries to have lunch with a higher-up. But the higher-up invites one of those guys (let’s call him Staunch #1), and he still makes Issa make some concessions if she wants to put on this show. Again, at this point, I’m not sure what the show is or what type of company Staunch #1 even works for. 

We then find out that Issa is trying to give the company she’s consulting for (???) a show put on by Crenshawn–an apparent fashion designer. When Crenshawn gets the notes that take a slice of South LA out of the show, he’s very upset and wants to drop out, but Issa convinces him that everybody has to make concessions when climbing the ladder. He seemingly agrees. At this point, I’m pretty sure he’s a fashion designer, but the way they talk about the show almost suggests it’s more of a musical performance. Perhaps that’s my own bias confusing me, but I was confused. 

On the day of the show, in true “Insecure” upset fashion, Crenshawn pulls a fast one and tells Issa that he’s moving forward with all of the things the company wanted out of the show. Issa is pissed, scared, and mad that Crenshawn calls her a sellout in the process. The show happens, it has a lot of surprises, and you can see that Staunch #1 is having an out-of-body experience just watching this. Now, I don’t know if I was influenced by Issa cringing as she watched the show go over the top with every element her client did not want in the show, or if I genuinely was taken aback by just how eccentric the show was, but even I thought Crenshawn went way too far into his bag for this presentation. 

Yet, to everyone’s surprise, Staunch #1 approaches Issa and lets her know that he loved the show and that it was exactly what his company (which I now believe is a water company) needed to be a part of. Issa is congratulated and rewarded for going through with the true vision, even though it was entirely forced upon her by Crenshawn. 

That whole setup is definitely a very mixed bag of adult life that gets thrown at Issa. First, there’s the element of selling out. By taking notes from Staunch #1 and asking Crenshawn to downplay his fashion show (I’m pretty sure that’s what it was), was she indeed selling out? Or was she simply the one that was able to guarantee the bag for Crenshawn that would give him a platform to do what he does, even if it meant tapering it to some degree? I think Black people across Corporate America face this all the time. It’s hard not to have very different ideas about how things should be done, oftentimes, as the lone Black person walking into a corporate office meeting, and yet, I doubt most of us throw out our most innate ideas for fear of not fitting in. Is that selling out? Or is that biding your time so that you can reach a position to do what you really want and enable other people to do what they want to do as well. 

And second of all, there’s a specific type of “growth”, which is in the title of the episode, that is rarely in a lot of “Insecure” episodes. Issa is now dealing with big boss decisions and consequences, and so now there’s the question of whether she’s really prepared for this big boss life. That’s ultimately the question she was asking herself during that panel at Stanford in the first episode–is she ready for the entrepreneurial life she signed up for? In the first of her corporate rough patches, we don’t quite know if she is. 

Molly’s Romantic Life

Molly’s professional life is seemingly well. During the earlier montage, we see her taking on extra responsibilities at work, much to the pleasure of her colleagues, who no longer seem annoyed by her presence. But perhaps for the first time in the history of “Insecure”, Molly’s romantic life has been put on pause as she and Issa have been working on their friendship with one another more so than any other relationship. 

But Molly realizes it’s time to get back out there. So she decides to join “The League” app again. As she tries to update her profile, she realizes just how overly demanding she had previously been, and the show helps us out with a montage of Molly’s previous relationship mistakes. In recognition of these mistakes, Molly decides to create a much more toned-down profile. 

But needless to say, her retreat from men appears to have been long and very bothersome to her mom. Molly’s Mom spends the better part of the episode trying to hook Molly up with random millennial-aged men. Her mom’s biggest push is a preacher who turns church songs into trap music. Molly politely declines this suitor. 

After attending Issa’s show (fashion show, right?), Molly goes on a date with a normal, cool-appearing guy. While we don’t know what happens on the date, her approach to it seems to suggest that she’s ready to be a lot more mild-mannered about her approach to dating. 

Issa’s Romantic Life 

Issa has also put her insecure romantic life on hold. When we last saw her with Lawrence, she was breaking up with him, suggesting that she wasn’t ready for the complicated relationship that Lawrence was likely to have ahead of him given Condola’s (apparent?) pregnancy. 

We see her talk and kick it with Nathan a couple of times on the professional level, but viewers out there knew it couldn’t possibly stay professional and/or platonic. After her event, feeling both lonely and tired, Issa calls Nathan, who we are to believe may have a girlfriend, over to her apartment to hang out. The biggest reason for calling him is probably to re-run what happened with Crenshawn over again and address the fact that part of her does feel like a sellout. However, after Nathan proclaims he doesn’t think Issa’s a sellout, Issa asks Nathan to stay the night. As Nathan gets in the bed with Issa, he makes a move to kiss her, but Issa bursts out crying, saying something to the effect of, “I thought I was ready.” 

What did Issa really want from Nathan? Maybe she was just in search of companionship. Then again, she and Molly have shared that. So one may believe she was in search of the companionship, or perhaps the intimacy, that specifically exists between a man and a woman? I don’t know. I’ll admit, the foolish male in me originally thought this was about Lawrence. Meaning, she wasn’t over Lawrence and couldn’t see herself moving on to Nathan. But after further thought, and more intelligent opinions from the fairer persuasion, it’s clear that Issa just wanted an intimate relationship. Because she clearly didn’t just want intimacy–she could have had that with Nathan. And I think if she posed that to Nathan, he would’ve given that to her–even if only for the night, but possibly for the foreseeable future. 

But really what she wanted was intimacy with someone that was 100% into having an intimate relationship with her. Nathan, quite frankly, has another woman in his life, and given the title of this episode, “Growth, okay?”, perhaps Issa’s crying was a result of realizing that starting off a relationship in this manner, intimate or not, was only going to lead to yet another bullshit dramatic affair, not unlike the many relationships she’s experienced throughout “Insecure”. On top of that, the piece that I think makes her cry, is also realizing that she’s been so hurt in her past relationships that she really doesn’t know if she can truly be the intimate person she wants to be. 

Obviously, we’re going to find out if Issa can find that intimacy before the season is over. Clearly, Nathan is all about providing some of it. But certainly, as the previews suggest, we haven’t seen the last of Lawrence, so he will re-enter the picture. 

Not to take anything away from the incredible learnings we received from Molly, Issa and how their personal growth may have affected their pursuit of love, but the end of this episode does give us that “will they or won’t they”, “Nathan vs. Lawrence” vibe that admittedly we’re all dying to know. Nathan and Lawrence are seemingly both great guys, but who she chooses might be a direct result of how Issa grows. Is she ready to take control of a relationship, go after what she wants and not let anybody else’s baggage way her down? Or is the desire for a fresh start with someone who hasn’t proven all that reliable in the past be both what she needs and what she decides she can handle? 

I don’t know, but thankfully, we’ll find out over the next few episodes of “Insecure”.

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