Let’s Talk About Issa

Last year, I took a stand and defended the complex and nuanced relationship Lawrence had with Issa, and himself, in HBO’s hit show, and the one program guaranteed to be the cause of several break ups, Insecure. It was long. But I think it provided a good lens on some important issues.  Now, I’m back to talk Season 2.

The first essay focused on Lawrence.The second essay focused on Molly. This is the final installment in my trio of thinkpiecery thoughts.

Issa (Issa Rae) and Daniel (Y'lan Noel) in a scene from the 2017 HBO dramedy series, Insecure.

Issa’s arc this season has been at once gratifying and sad. While Lawrence drifts through life with all lacking of intentions, Issa is quite the opposite: every move she’s made has been fully intentional, for better or worse. The problem with this is that she’s about as experienced in ho-life and emotional stability as La Narañja is in being a president. (Lowkey, who can blame her though? Ho may Be Life, but it’s also hard. And adulting is even harder.)

Take for instance her brief episode at work.

Instead of being a strategic professional and reporting the racially-tense dynamics to her boss at We Got Ya’ll, Issa handles everything on a tactical level, hoping to score an easy win, at the expense of her company and her own position. What follows is a swift comeuppance that – despite how much I hate every white, bleeding heart at We Got Ya’ll – was deserved.

While these cut-aways to WGY and Issa’s professional life are often lacking much structure, they do provide context for the decision making process that Issa employs throughout S2: “Troublesome situation arrives? Let me selfishly act on this with abandon. I will not think about larger consequences because I’m too caught up in what X person thinks of me and/or what I think of myself in this very moment. Things will be fine. And if they’re not, I can lash out while simultaneously falling into a cycle of self-loathing, hoping someone will feel pity for me.” (Author’s Note: I’m only partly joking there. Emphasis on partly though.)

A good illustration of this is Issa’s “be shitty to everyone in my roster” arc: from assuming that Big Ol’ Forehead Neighbor Bae is just on-call for her, to misreading Latino Bae’s intentions and being Awkwardly Hoeish, to yelling at Daniel an episode later for a natural conclusion to a competent blowjob. Issa’s solution to heartbreak is to fuck her issues away and act as impulsively as is humanly possible because, why the fuck not? It’s the go-to solution that’s been bored into so many of us via society, but Insecure works to show that it’s often the wrong (initial) move, and not a cure-all for heartbreak or directionlessness.

On a macro level, it’s a bold narrative move that challenges the popular, empowered pseudo-feminist/”woke” rhetoric du jour. But, it’s also definitely heavily tinged with conservative thought: no hoeishness goes unpunished in Insecure (except for Kelli’s, but she’s a tertiary character and is just now becoming relevant). Much like the black community itself, the show leans left from the center right on most issues. It’s a fascinating thing to be seen played out in everyday life of a (black, female) character with such (at times grating) self-awareness, especially when dealing with hard facts of life. 

But I’ve digressed…

Issa’s downward spiral is not unique to her, or to anyone who’s been through a breakup. In fact, it has a particular bit of resonance because she is a black woman who’s experiencing a fuller range of humanity than most are allowed on the boob tube.

When we talk about wanting to see fuller, more realized black woman characters on the screen, we often forget that “fully realized” means “fully realized,” warts and all. And, like a Being Mary Jane, Insecure has made no bones about making us love and hate Issa in the journey. Note that’s not a moral assessment. Rather, it’s a call to meditate on the fact that in order to enjoy this diversity, we also need to enjoy the discomfort we may feel at not liking a character because they reflect our own dark, very human moments.

Issa (Issa Rae) standing alone on a sidewalk, in a scene from the 2017 HBO dramedy, Insecure.

Building on this, some may feel like S2 was much kinder to Lawrence, allowing him to make mistakes that often didn’t lead to material downfalls, while Issa’s life fell off the ladder of chaos, down into the bottomless pit. But I’d argue that they’re equal, and on par with the show’s myriad themes of heartbreak, depression, loneliness, inexperience and general shitty moments we all feign to not experience when we post overly cheerful and filtered pics to IG.

In S1, Lawrence started at the bottom, having next to nothing besides Issa. And, his journey has only been a sideways one. As the story progressed in S2, he’s traded homelessness and joblessness for an empty hole in his heart with a rotating cast of Not Issas. In turn, Issa technically had everything: friends, job, home and car, and Lawrence….on the couch. But, as her descent into heartbreak and depression accelerates, she’s equally alienated from her workplace, friends and bad luck greets her aggressively, like a Kappa pledge in their 8th week on line. The trading places-ness of these arcs illustrate this season’s meta-narrative at hand, while also solidly illuminating how detaching emotionally, physically and sexually from someone just fucks you up as a person.

The latter centers heavily on emotional instability and mistakes. Issa and Lawrence both lash out – fall into self-destruction and depreciating sense of self – and act with increasing unpredictability; their decisions rooted in comfort and attention over healing and introspection. They trade in superficial bandages to deeper wounds, leaving themselves vulnerable to general happenstance and much more insidious forms of Murphy’s Law.

It’s part of why that argument outside of Derek’s dinner party is so visceral. In those moments, their pain is at once shared and singular to the inflicted. Lawrence sees and surmises from scant info provided outside Issa’s world, and is thoroughly crushed by it. In turn, Issa sits within a realm of fantasies and advice, at once not sure of if she wants Lawrence and constantly needing him (and others) to validate her pain. This need for validation is shared between them, to an extent, and speaks to the Insecure‘s dialogue on co-dependency. Despite the breakup, Lawrence and Issa’s love is both broken and half-made. At their best, they were inseparable. But at their worst, they’re also inseparable. The very bonds that made them so in love are the hooks and chains that bind them, preventing either person from moving on and/or healing.

This is best highlighted in the finale when they trade apologies. Lawrence realizes and expresses his inability to let go of arbitrary enoughness. In turn, Issa expresses regret at how she acted but also at how she couldn’t be enough for them both. This is dangerous because, while it may have rang true, it highlights how their codependency – their inability to be singular people, who do things for themselves and not just for each other – is what holds them back.

This is furthered by Issa’s daydream of a repentant Lawrence who wants to wife her up on the spot. While it can definitely be read as a mourning of what should have been, it’s also a fever dream of Issa’s own insecurity: despite all these moments and movements, deep down she still wants what she thinks should be because – at the moment where she’s at her lowest – she doesn’t feel like her life is enough on its own.

Granted, this is my interpretation, because the subsequent scenes throw a bit of ambiguity into the mix. Maybe it was a resolution for Issa. Maybe Lawrence wants that too. We really don’t fucking know. And that simple fact is profound, especially as it’s matched with Lawrence re-friending Issa on Facebook, who smiles in the cab…on the way to Daniel’s house. What does this mean for her rebuilding trust with Lawrence? We know they’re both in love. But what of Daniel? What is his say or stake in the matter? Will this continue to be a star-crossed lovers tale?
Issa (Issa Rae) and Lawrence (Jay Ellis) married, on the couch, in a daydream sequence from the 2017 HBO dramedy, Insecure.

The beauty of Insecure is that it stakes its deepest dramatic pulls in inverting popular and traditional (both old guard and nouveau) notions. In the case of star-crossed love, Insecure seems to suggest that being fated for one another in 2017 isn’t sexy, because it’s often just romantic co-dependency and toxicity. “Finding your way back” to someone instead of starting with yourself is a surefire way to hurt a lot of people. And if these two seasons have shown us anything, it’s that pain is cyclical when Issa and Lawrence are involved.

This isn’t to say that they can’t change. Rather, it’s that their issues are between them. And until they handle it as such – alone, together, etc – anyone caught in between them will be in dire straits emotionally, sexually, etc. It’s a frightening concept when it’s put in plain English, but it’s the truth the show puts into action nonetheless.

Going into this season break and beyond, I hope we all sit down and take stock of these messy lives and how they reflect our own, for better or worse. Not to be guilty of our choices and mistakes. But to better understand how we’ve come to where we are and how we can avoid looking like Boo Boo The Fool in the future. Because we can be damn sure that the whole cast will be clowning it up come Season 3.


these boots mine.Dap owns Timberland boots and is committed to loving black women, eating good food and diversifying media as he sees fit and while he can. He can be found yelling into the abyss and being snarky on the following:  IG | Twitter