Is Insecure Preying on Black Women’s Insecurities?

Issa Rae
Issa Rae

I may lose some friends over this.

In fact, I may lose friends, followers, respect and possibly even my “black card” (which, apparently, has been under review since I dared address the Nate Parker issue). Which is unfortunate, since being black is one of my favorite things, and one of my favorite things about being black is enthusiastically cheering on other black folks—especially black women, of whom I am one.

However, one of my favorite things about being a black woman is not simply bowing down to any and all iterations of #BlackGirlMagic, but trusting my personal community of sistren to enlighten, check and call me out when necessary. Which is why I’m willing to dust off my lounge chair and find a sunny spot on what my editor aptly calls “Unpopular Opinions Island” to offer an honest critique of one of this season’s most anticipated and already beloved series: Issa Rae’s Insecure.

Now, before any righteous indignation pops off pre-emptively, let me say this: When I learned that HBO was releasing the pilot two weeks ahead of the series premiere, I was hyped (if you’ve yet to catch it, you might want to stop reading now, because … spoilers). In fact, I’d been hyped off the promos for months beforehand. And when I discovered that journalistic privileges would give me access to the first six episodes? Yes, please.


For those unfamiliar, Rae’s entertaining and highly popular YouTube series, Awkward Black Girl, had long since established her as a refreshingly offbeat yet relatable voice, well deserving of the platform HBO has now given her. Like many of you, I couldn’t wait to see how that voice would evolve, once afforded the budget and publicity that one of the world’s biggest premium cable networks could provide.

And indeed, for those who loved Awkward Black Girl, Insecure feels like greeting a good friend after a long absence; many of the same themes are explored, and there are even a few familiar faces. It hits several sweet spots in conveying the contemporary black millennial (and, in large part, Generation X) experience: the fine art of code-switching, the sisterhood of black female friendships and, poignantly, the challenges facing a generation whose education increasingly outpaces the opportunities available to them.

But as clever, candid and chuckle-worthy as the pilot is, something disturbing seems to have happened on Rae’s way from the web to HBO. Our adorably awkward black girl—whom so many of us identified with as our own alter ego—is still present and entertainingly awkward, but now she’s also perpetuating some of the most clichéd and damaging stereotypes about single black women in America.

The primary vehicle for this trope is Rae’s character Issa’s best friend, the chronically single Molly (whose name I admittedly hoped would be spelled “Mali” because a black girl named Molly sounds like a sitcom unto itself). Molly (Yvonne Orji) is the type of black girl who seemingly has it all: beauty, brains, personality, a rapidly excelling law career and a flawlessly attired ability to navigate disparate aspects of her life with enviable ease. And yet, what plagues her most is her inability to attract and sustain a relationship … at least, with a man she considers to be of her caliber.


At first her honesty and vulnerability about this is refreshing and relatable … until we learn that Molly’s compulsion to be coupled prohibits her from even celebrating the romantic successes of others. To make matters worse, Issa—herself in a dissatisfying long-term relationship—seems to blame Molly (and her “broken p—sy”??) for her singleness. By the time she publicly exploits Molly’s pain for entertainment, I couldn’t help feeling a bit betrayed myself, as painfully familiar visions of single and stereotypically bitter black women danced through my head …

After all, we’ve heard this story before, haven’t we? In fact, heterosexual single black women have heard it repeatedly for years now: the statistics about our marriageability; our lack of desirability in the online dating arena; the lack of available and compatible black men; the urging that we lower our standards; the echoing tick of biological clocks in empty wombs. We field uncomfortable and intrusive questions from friends, family members and even dates (“So, what’s wrong with you?”). We shrug it off, talk about it among ourselves, form sister-circle support groups and, when necessary, swap coping strategies along with dating advice.


All of this is to say that Insecure isn’t telling us anything we don’t already know about being a single black woman with dwindling prospects and advancing years. But is casting singlehood as the worst-possible outcome really a narrative we need to keep promoting?

Having now watched most of the first season of Insecure, I won’t divulge any further spoilers here, except to say that it gets better. It also gets worse. In fact, as the season progressed, I was both surprised and troubled to frequently find myself empathizing more with the male supporting characters than with either Issa or Molly, despite sharing both a gender and more than a few experiences with them.


And I get it: In lieu of representation on prior HBO hits like Sex and the City and Girls, Insecure is a long-awaited breakthrough—albeit one that occasionally feels like Girls in sepia. And after decades of either nonexistent or woefully one-dimensional black heroines on the small screen, recent years have brought us several dynamically flawed “sheroes,” most notably Olivia Pope, Annalise Keating and Mary Jane Paul (another tragically single career woman), all of whom are at turns sympathetic, yet often difficult to root for. Even new hits like Greenleaf and Queen Sugar feature multifaceted women with fluctuating moral compasses.

And while this is both refreshing and real, I can’t help wondering: Do we really want or need a black Lena Dunham (when one already feels like plenty, to be honest)? And, more importantly, do we really want to reinforce for yet another generation of black women that—shoutout to Billy Dee—their success is nothing without someone to share it with? Don’t we already know that line by heart?


Insecure is well worth the watch, but I dare say it could do better by us. Rae may be strumming our pain, but the song she’s singing about our lives is feeling a little played out at this point.

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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