We Are All Insecure

Lawrence (Jay Ellis) and Issa (Issa Rae) in HBO’s Insecure
HBO screenshot

Eight weeks ago, The Root published an article I wrote, titled, “Is Insecure Preying on Black Women’s Insecurities?” It was a simple question, based on an honest concern I’d had while previewing the show prior to its debut on HBO: As viewers—and, at times, voyeurs—of Insecure, what was our intended takeaway? Was there a deliberate implication that simply getting and/or keeping a man is the endgame—respect and happiness be damned?

Unsurprisingly, I sparked some righteous indignation by even daring to ask—or perhaps for writing anything other than a wholly glowing review—despite my enthusiastic and ongoing praise of the show’s creator, Issa Rae. For example, a typical clapback might read:

“Damn, it’s fiction. Why do you need to psychoanalyze it? Sounds like you’re projecting your own insecurities onto the show.”



Fair enough. As notorious “gonzo journalist” Hunter S. Thompson once quipped, “There is no such thing as objective journalism.” For an op-ed writer, objectivity isn’t even an expectation. Despite desperately wanting to, I’d had trouble latching on to some of Insecure’s storylines and had chosen to say as much. And while I’ll neither disavow nor double-down on it now, frankly, I was surprised that my critique even caused so much as a ripple in a sea of otherwise overwhelming praise. Mine was simply an unpopular opinion. End of story.

But weeks after the fact, I was still being asked to discuss and defend my stance—among friends, to Facebook groups, even on the radio. More surprising? Clandestine messages of thanks for publicly expressing an opinion that, while unpopular, was ultimately not mine alone.

I suppose that’s why I was asked to revisit it: Because fiction or not, it was clearly a loaded topic, apt to strike nerves. But isn’t that the objective of art? By that measure alone, Insecure has been a tremendous and immediate success. So what does my opinion matter—especially if presumed to be based on my own latent insecurities?


Hell, maybe I was just wrong. I’ve been wrong before.

But having already watched six of the season’s eight episodes prior to Insecure’s premiere, it was with studied detachment that I watched the series again in real time, while closely following the feedback on social media. I was interested to see if my initial impressions would be echoed or challenged. Perhaps there was something I’d missed—or somehow misunderstood—the first time around?


As it turned out, there was.

The action and dialogue remained unchanged, and occasionally cringe-inducing. But through the lens of my peers, something else became clear: Despite the numerous “flawed” black leading ladies who have appeared on our screens in recent years, in “Issa” and “Molly,” Issa Rae has somehow created female characters who, while often unlikable, are nevertheless disturbingly relatable.


After all, the vast majority of us aren’t having scandalous affairs with sitting presidents while manipulating the Washington, D.C., political machine, or teaching a gang of dysfunctional legal eagles how to (repeatedly) get away with murder. We’re typically not even high-powered basketball wives-turned-queens of sugar plantations, or successful-yet-reckless news anchors trying to balance our ravenous ambition and longing with just being ourselves … whoever that may be.

No, most of the time, we’re just like Issa and Molly: “professional black girls” (shoutout to Dr. Yaba Blay) working, living, striving, loving if/when we can, and trying to keep our sanity and hope alive in the real world, a world that struggles to recognize our humanity, let alone our brilliance—even while appropriating it.


And yes, part of that humanity is awkward, messy, hell-bent on self-sabotage and insecure AF.

As the season progressed a second time (for me), I was admittedly gratified to see some of my friends struggle as I had, trying to reconcile their desire for these characters to win with an equal desire to shake them until their eyes rolled back in their heads. But by the time Molly's and Issa’s issues reached an inevitably ugly climax in episode 7 (aptly titled “Real as [F—k]”), there was little to no satisfaction in finally hearing my misgivings confirmed by the characters themselves.


Molly: “Bitch, you don’t even deserve Lawrence.”

Issa: “Are you mad that I can actually keep a [n—ga]?”

Sigh. Not like this, y’all. Not like this.

And as it turned out, keeping him wasn’t even in the cards, was it? For many, Sunday night’s finale culminated in the formations of “Team Issa” and “Team Lawrence”—ironically, forcing us to once again choose between the “lesser of two evils” for the second time in the space of a single month. Personally, I’m not interested in weighing the morality of either, because I don’t believe that Issa and Lawrence’s relationship is the glue that holds Insecure together—which is why the closing scene is so poignant.


But despite the seeming absurdity of picking sides in a fictional war of the hearts, what has been sparked is a much-needed real-life conversation about realistic expectations, surviving betrayal and the limits of loving relationships. And all betrayals considered—and to be clear, they extend far beyond Issa and Lawrence, and all the way back to episode 1—I wasn’t terribly shocked by the finale. If you’re honest, I don’t think it surprised too many of you, either. Enough of us have actually been privy to that scenario to know that scene (you know the one) was one of the realest moments of the entire season. After all, as the saying goes: “Hurt people hurt people,” right?

And if anything, that dose of raw reality may be what I missed in my first viewing and analysis of Insecure—however constructively intended. Yes, there are problematic and occasionally predictable tropes in play, some of which I’d still like to retire. And no, I’m still not entirely sure I’d want any of these characters as a friend—or a significant other. But while Insecure’s characters may not be universally likable, in them, our messiest and most selfish selves are both reflected and strangely validated. However flawed these characters may be, they’re rooted in uncomfortable—and undeniably black—truths, making their impact ultimately far less arbitrary than empathetic.


Maiysha Kai is a Grammy-nominated singer-songwriter, fashion model, devoted auntie and Brooklyn, N.Y.-based, single black bombshell who recently strutted into her 40s. She is also an expert at oversharing who chronicles her attempts at dating—and adulting—on 40onFleek.

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