Hella Homecoming: The Evolution of Insecure


Summer is indisputably a season tailor-made for black joy. ’Tis the season of cookouts, stoop-sitting, rooftop bars, music and food festivals, block parties, hand fans, summer jams and all-white affairs (“Diner en Blanc,” if you’re bougie).


And for fans of Issa Rae, it is now also the season to welcome with open and sun-kissed arms the return of her hit series Insecure (which merited a block party of its own last Saturday).

Frankly, with the level of excitement and anticipation generated by the release of the trailer alone, I was mildly surprised that the promotional campaign didn’t adopt the tagline “Summer Is Coming” (shoutout to another HBO fave, Game of Thrones). Because while this year’s Emmy-nominating committee may not have felt the love (clearly, it didn’t get the memo from the Golden Globes), come Sunday night, a huge swath of black America will be eagerly settling into our respective “bouches” to see what’s new and next with Issa and Co.—which is exactly what I did on my summer vacation.

Spoiler alert: This season is hella fun to watch. Malibu. (Yes, they’re actually trying to make “Malibu” happen. Get with the program.)

That said, I approached my second Insecure review with equal parts anticipation and trepidation. After all, last season, I garnered a substantial amount of shade for daring to express the unpopular opinion that HBO’s freshest show was perhaps a bit too heavy-handed in perpetuating stale stereotypes of single, successful black women—namely, that we’re too thirsty to consider ourselves complete without a man in the picture. (Fun fact: You can think something is great without thinking it’s perfect.) With season 1 ending with both Issa and Molly unwillingly alone, would there be more self-flagellation on the menu?

But if season 2 reunites us with the crew almost exactly where we left them last fall, it now handles its heroines with a both gentler and defter hand, adding significant self-awareness to its sophomore stride.

Expectedly, our eternally awkward black girl is now trying to navigate life after Lawrence (Jay Ellis), grappling with both a “broken pussy” and a broken heart after her dalliance with Daniel (Y’lan Noel) has effectively destroyed their five-year relationship. It’s a reckoning rarely explored from a woman’s perspective, and the results are simultaneously heart-wrenching and hilarious.

Meanwhile, Molly—easily the best-written best friend currently on TV—is taking a more compartmentalized approach to life after her series of disappointments in season 1, opting to focus on her career rather than her relationship status. It’s an extremist approach, but one that most career-driven women can relate to after weathering enough romantic disappointments. And yet, even without men in the picture, life ain’t automatically no crystal stair. As Molly’s new therapist—a rare maternal figure in Insecure‘s sea of black millennial angst—acknowledges:

[A]s black women, it can feel like there’s a lot of things stacked against us: We feel invisible at work; we feel the need to have the perfect relationship; it’s a lot. But if your “shoulds” didn’t come to fruition, would you be open to your life looking a different way?


And it’s the “shoulds” that take center stage this season as our cast continues to struggle with insecurities and expectations about where they “should be” as they approach their 30s (a struggle that I can personally confirm doesn’t end with your 30s). And thankfully, those insecurities remain equal opportunity; Lawrence may no longer be Issa’s other half—or the dude best known for his presence on the couch—but he’s still got his own identity issues to deal with; namely, what really constitutes being a “good dude.” (Hint: It doesn’t just entail having a job, a functioning penis and a basic grasp of monogamy.)

Insecure’s stellar supporting cast is back for more, too—along with some fun guest appearances—and given ample opportunity to shine. The cohesion and chemistry have only become more solid this season, to hilarious effect. In particular, Natasha Rothwell’s standout return as Kelli (as well as a writer for the show) sets this season off with consistent and impeccable comedic timing, stoking this writer’s excitement for how her own HBO development deal might pan out.


Even four episodes in, it’s fair to say that along with the sophistiratchetry we’ve come to know and love from this crew, there’s also plenty of self-reflection to look forward to this season. Balancing the need for independence with the need for intimacy; working out our own racial hypocrisies under the earnest and oft-patronizing gaze of white allyship; sex for sexuality’s sake (as opposed to a vehicle to relationships); the inequities that often accompany being black and female at work; the reality that there’s no reliable route to a happy ending; and the disappointment that sometimes comes with getting exactly what we want are all up for analysis, and the result is ... refreshing.

And as for my prior unease about the story Insecure might be telling about single black women? Well, perhaps that concern is best addressed by Molly:

“Damn. I was out there like that?”

Clearly, just like the rest of us, she’s learning from her mistakes. Because what’s the point of admitting our insecurities if there’s no evolution?


Insecure’s second season premieres Sunday, July 23, on HBO at 10:30 p.m.

Maiysha Kai is managing editor of The Glow Up, host of The Root Presents: It's Lit! podcast and Big Beauty Tuesdays, and your average Grammy-nominated goddess next door. May I borrow some sugar?



I am so excited for this and I don’t know whose story arc I’m more interested in: Issa, Lawrence or Molly. Issa is so relatable in the show but Molly reminds me of myself. Hard exterior but really just scared inside. I think Molly is going to come into her own this season because I think she’s ready to embrace herself but you know that she’s going to struggle along the way. And Lawrence has gone through some shit with Issa. It will be great to see him navigate manhood without Issa, even though I know they shouldn’t get back together (at least right now).