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Insecure Reflections: On Being Team Molly, If That Even Matters

Like many of you, I’ve been using my newfound time during lockdown to catch up on some of the TV I’ve missed out on over the past couple of years. One of the first shows on my list was Insecure, which, if you haven’t watched it yet, is just as good as everyone has told you it is, and I devoured all 34 episodes in less than a week. Season four may have ended back in June, but I am here to once again throw my belated opinion into the mix, if only because Team Molly appears to be short a few players. That’s right, you heard it here first. TEAM. MOLLY.

(Minor spoilers for Insecure to follow)

Okay, I’m actually not going to be that intense about this because honestly, both Issa and Molly are incredibly well-rounded characters with as many positive attributes as they have flaws, which is part of what makes Insecure such a good show in the first place. What I mean when I say I’m Team Molly is that I relate to Molly in a lot of ways, and the things that frustrate her about Issa are things that tend to frustrate me both in friendships and relationships.

One of the main criticisms Molly receives on the show, not just from Issa but from other friends and even partners, is that she’s too negative. Molly’s negativity is something she at first refuses to recognize, but once she realizes that it’s a real thing and it’s depriving her of joy, she starts to work on it in therapy. 

As a person who many would have formerly described as “negative” and who many would now describe as “mixed to positive,” I really felt for Molly, especially during that first season. In my own experience, pessimism isn’t something I have to strive for, but something I have to work against. I don’t know if it was something in the way I was raised or if it’s simply in my nature, but being a downer about stuff comes naturally to me. I had this pointed out to me a number of times when I was younger, but it was always something I laughed off. “That’s just the way I am” was my common refrain, and sometimes I even took a weird sort of pride in being so cynical. Of course, a healthy dose of pessimism is crucial when it comes to processing the often unfortunate experience of being a human being, but when people are telling you that the way you see the world is negatively affecting the way they see the world, it’s time to reassess what is not actually a personality trait but a self-destructive thought pattern. 

All of this is to say… Molly is going through a pretty similar journey to my own in terms of acknowledging and then working to correct her excessive negativity. She’s still working on it in season 4, and I’m still working on it in whatever the hell season of my life I’m currently in.

Issa, on the other hand, is not a negative person. She is an encourager, the type of friend you’d go to if you want someone to hype you up or assure you that the subpar idea you had is actually a really good idea. She has the best intentions, but she goes about things in a way that is diametrically opposed to Molly’s way of life. Molly likes to have a plan, and Issa is not a planner. Throughout the series, we see Molly’s frustration with Issa’s ability to stick to a plan, whether it’s her plans for her own life and career, or the plans they make together. Issa tends to let the wind carry her in any direction it takes her, not considering the consequences her flighty tendencies might have on other people. 

If there is anything that I can’t stand in a friendship, it is being unable to rely on a person. Obviously every person has their bad days and there are always exceptions to the rule, but to me, routine flakiness implies a lack of consideration for other people. And so, as the central conflict of Insecure’s fourth season ramped up, and I watched as Issa repeatedly flaked on the plans she and Molly made to discuss the tensions in their friendship, I felt more and more inclined to side with Molly. 

Issa obviously has reasons to be upset with Molly, too — Molly’s refusal to connect Issa with Andrew seemed to come more out of a place of pettiness than genuine concern about how it might affect her own relationship with Andrew — but at the root of it, from Molly’s point of view, Issa has neglected their friendship instead of trying to nurture it. If a relationship matters to you, you’ll put in the work to keep it going even when times are tough, and Issa would rather avoid it altogether. Issa simply doesn’t care enough to try to fix it — or at least, that’s how Molly feels, and how I would too if I were in this situation. 

There are two sides to this, but that doesn’t mean we have to choose one; in some ways, being staunchly Team Molly or Team Issa dilutes Insecure’s conscious efforts to show us both perspectives. The show gives Molly and Issa almost equal time and consideration, even if it ultimately frames Issa as the protagonist. The fact that there is a Team Molly at all is just further proof that Issa Rae and Larry Wilmore are succeeding hugely at telling the story of these characters, who are so three-dimensional in their nuances, their worst qualities and their moments of grace, that I feel like I know them both in real life. Being able to see that both sides exist and are valid is what matters more than deciding which side we ultimately fall on.

That being said… Team Molly tho.