Know-Better Blues: Why Insecure Is TV’s Best Show About Thirtysomethings

At first, the new season of Insecure suggests a study in contrasts: When Molly (Yvonne Orji) returns to L.A. from a luxurious getaway, eager to start work at a new, black-owned law firm, Issa (series co-creator Issa Rae) agrees to scoop her from the airport—and Molly hops in the back as if she were a fare. It’s a gag, of course—the pair’s bright peals of laughter are as central to the series’ sound as music supervisor Kier Lehman’s effortlessly hip song selections—but it’s one with an edge, as Issa, hard up for money, has been driving for Lyft after work to earn extra cash. It’s a metaphor, it seems, for their respective trajectories: Molly is once again on the rise, optimistic (if imperious); Issa is once again uncertain, sleeping on an old flame’s sofa and struggling to be heard at work.

But Insecure isn’t in the business of fulfilling expectations. In fact, if there’s one feature that can be said to define the series—and that distinguishes it from the traditional sitcom, to which Season Three explicitly refers—it’s an openness to change, to the swerves and switchbacks by which its particular slice of modern black life doubles as the medium’s most pungently funny portrait of thirtysomethings: Insecure captures the feeling, as The Outline’s Brandy Jensen so impeccably puts it, of being “late to your own life,” then expands the thought to the length of a TV series. Which is why it’s telling that Molly and Issa, despite the appearance of a major gulf in their outlooks, both use the same phrase to describe their own—and the series’—ongoing transformations. “I’m on some ‘know better, do better’ shit,” Molly celebrates early in the season premiere, the title of which, “Better-Like,” already contains its own hedge. “I just think we know better,” Issa says later, as Daniel (Y’lan Noel) moves in to kiss her, setting off a sudden chill in the room. In Insecure, as perhaps in life, to be 30 or 31 or 33 is to confront a case of the know-better blues: The keen and often dispiriting sense that learning from your last mistake doesn’t mean you can prevent yourself from making the next one.

If 40 is indeed the new 30, then 30 is the new 20 (ish), and the profound flux that accompanies it is built into Insecure from the ground up: By the end of “Fresh-Like,” the fourth and last of the Season Three episodes made available to critics, Molly complains to her therapist that she’s had to return to square one at her firm, and becomes embroiled in the office politics she spent Season Two trying to escape; Issa, for her part, enjoys the intoxications of a “fresh start,” including a new love interest, Nathan (Kendrick Sampson), himself in the midst of a major transition. It’s this role reversal, in the space of the season’s first half, which underscores one of Insecure’s central insights about its characters’ age, or at least the one that codes most closely with my own experience. Though I never dreaded turning 30, it left me reeling nonetheless: My successes and setbacks since then have seemed newly consequential, the pressure to reach certain milestones more suffocating than ever, even though I know better, or should—that my dearest friends, nearly all of whom are in healthy, long-term relationships, don’t feel as if they’re coasting simply because their not single, any more than I’m coasting because I landed the job of my dreams.

Insecure almost preternaturally understands this rhythm, not least because it’s propelled by the same tension between stasis and change. On the one hand, the series rests largely upon Rae and Orji’s relaxed chemistry, a consistent reminder that Issa and Molly have been friends since college. On the other, it swiftly (and not unrealistically) dispenses with Issa’s ex, Lawrence (Jay Ellis), as soon as he drifts too far from her orbit. In both cases, the result is the same: Insecure positions itself as the polar opposite of this season’s hilarious show-within-a-show, Kevin—a Martin-inspired sitcom that’s been revived à la Will & Grace—by embracing, rather than rejecting, its own evolution. “Li’l Chris, 45 years old still hidin’ in cabinets,” Issa quips in the season premiere, as she and Daniel ease their know-better blues with a flurry of laughter. The moment is a self-conscious comment on the ways TV series change (or fail to), but by extension, it’s a comment on the ways we change (or fail to) as well: In Insecure, indeed for Insecure, there’s no more merit in being dulled by habit than there is in being terrified by change.

To wit, Insecure doesn’t allow us much time to get used to the transformations brought by the second season before it presses forward in the third, even as it acknowledges that our oldest patterns die hard. Molly tries to fit in at her firm, and to figure out what to do about her (married) paramour, Dro (Sarunas J. Jackson); Daniel nabs, then sabotages, a chance to advance his career; Issa gets serious about her finances and fights to have her colleagues at We Got Y’all take her more seriously, only to come up against Frieda in a “J’ADORE EQUALITY” shirt—a sight gag is so brutally funny it almost blistered my pale-ass skin: The point is, there is no milestone in life—not 20, not 30, and presumably not 40 or beyond—after which one coasts along on having “figured it out,” a lesson Insecure rather admirably refuses to treat as self-evident. Because it’s not. Or, it hasn’t been to me. It’s nice that Rae and company recognize that knowing better is a key ingredient in doing better, but it’s not the only one.

In a season, a series, so unafraid of metamorphoses both large and small, it’s important to note that its most consistent through line, its signal motif, is the character Issa refers to as “Mirror Bitch”: a (literal) reflection of herself dating to the start of Season One. It’s for Mirror Bitch that Issa practices her art, that she preens and pouts and pep-talks, and her absence from Daniel’s house—where the bathroom has but a hand mirror hung on the wall, in which Issa peers silently at her squinched face—is as much an indication of Issa’s uneasiness—at Daniel’s, in life—as anything else. When Mirror Bitch returns, it’s as Issa grapples with what it really means to know better, which, of course, is to know yourself. She is demonstrably not “a brand-new bitch,” “a make-no-mistakes bitch,” as Molly claims, but she is an increasingly confident (dare I say secure?) bitch—and if such knotty self-awareness, intricate wisdom, is what awaits us on the other side of this upset, this flux, I suppose that’s a trade worth making. Pointedly, then, on the day of Mirror Bitch’s return, Issa discovers her high-school rap journal, homing in on the lines, “I got big dreams / I got big schemes / I’m never mediocre / About to take over.”

“Oh, Issa,” she says to her former self—still half optimistic and half uncertain, yet also transformed. “You were so simple then.”

We all were. It’s the often painful process of accepting change, with all its complications, that we call “knowing better”—which is just another way to say, “growing up.”

Season Three of Insecure premieres Sunday, August 12 at 10:30 p.m. on HBO.