Issa Rae’s HBO show is the most honest look at the anxiety and exhilaration of dating that we’ve seen in a very long time.

Issa Rae and Yvonne Orji in Insecure.

Issa Rae and Yvonne Orji in Insecure.


In the first episode of Insecure, Issa, played by Issa Rae, the co-creator and the star of the new HBO show, imagines a white colleague lecturing her about romance. “Educated black woman are highly unlikely to get married the more education they have,” this poltergeist tells Issa, in the middle of a staff meeting. “On the bright side, many black woman are work-focused and find happiness in their careers. But then there are a small percentage of pathetic women who have neither. They are purposeless.” Issa, a college-educated Los Angelina who works for the nearly all-white educational nonprofit “We Got Y’all,” is considering ending her long-term relationship and so particularly susceptible to this anxiety. Insecure looks it right in the face, a prestige comedy that takes wanting to be in a relationship as seriously as relationships themselves.

Rae is the creator of the beloved web series The Misadventures of Awkward Black Girl and has been trying to translate that to television for some years now, before co-creating Insecure with Larry Wilmore. As the title of her web series suggested, there is something of the superhero about Issa: not a superpower so much as a secret identity, a jokey, friendly exterior that belies a churning mind. Rae brings this quality to Insecure, where a running conceit has her rapping fiery pep talks to herself in the mirror, which she mostly ignores. Readying herself for a night out, she tries on multiple lipsticks, each inspiring a different personality, before selecting exactly none. She describes herself as “aggressively passive” and avoids conflict even when it would simplify things. She ignores uncomfortable situations and text messages. She nearly breaks up with her boyfriend but refuses to have a clarifying conversation with him when he spots her in a Rite Aid.

Co-starring in Insecure is Issa’s college best friend Molly (Yvonne Orji), a high-powered lawyer who grew up as a self-described “hood rat.” Molly, Issa tells us in voice-over, is beloved by both black and white people, as the camera shows her code-switching with the dexterity of a World War II morse-code operator. Insecure stars black characters who deal with white people largely as a professional necessity—just one of the things it shares this with Atlanta, Donald Glover’s new auteurist series on FX. Both shows feature a protagonist that white people nonetheless feel comfortable with: In the first episode of Atlanta, a white man nonchalantly uses the N-word with Glover’s character. Issa’s colleagues ask her what on fleek means, and in the show’s opening scene, a classroom full of kids wonders why Issa sounds so white and makes fun of her natural hair.

Insecure takes on racism directly, largely in a professional context. Issa’s white colleagues take to emailing behind her back about a project she is in charge of; Molly’s boss asks her to speak with a summer associate who refuses to code-switch. But just by being about black people living their lives, Insecure shows us, for example, a much more expansive Los Angeles than the claustrophobic one seen in white comedies set in Silver Lake (Casual, Togetherness, You’re the Worst, parts of Transparent). Issa and Molly brunch at hipster spots too, but Molly grew up around Florence and Crenshaw; Issa’s apartment is in Inglewood, near the old Forum. Theirs is a much bigger, more diverse L.A.

What stands out most about Insecure is not its matter-of-fact approach to race but its matter-of-fact approach to wanting a romantic partner. Issa and Molly are both, in their way, relationship-crazed. Issa is in a long-term relationship with Lawrence (Jay Ellis), a nice, seemingly dull guy, when she re-starts a flirtation with a high-school ex, Daniel (Y’Lan Noel). In almost any other show, she and Lawrence would end things—he’s pretty snoozy in the first two episodes—but she’s scared to be alone, and he gets written into a real character. They turn the corner, make it work, until, of course, other complications arise. Issa’s fear keeps them together, and that might be a good thing. Molly, on the other hand, is single and dating ferociously, if miserably. Not only is she meeting every joker on Tinder, she’s also having a hard time finding a man who is both up to her standards and not put off by her standards.

Especially for female-focused series, the shadow cast by Sex and the City remains long, dark, and full of Cosmos. Sex and the City was (and is) hugely popular, beloved, and serially copied, but its reputation has been tarnished by its materialism and its movies. A show about how friendship and work could sustain women, it is nonetheless understood as a kind of boy-crazy manifesto of aughts excess. It’s not just that Sex and the City’s comprehensive take on bad dates makes any kind of conversation about male foibles feel like a cliché, it’s that aspirational television—or really, aspirational feminism—has moved on. Empowered women don’t date every single attractive man in a giant metropolis to discuss what is strange about his dick over drinks; they don’t sweat romance at all, putting it in the background, preferring to focus on friendship. (This focus is also inspired by Sex and the City, the forerunner of all the shows about close female relationships, from Girls to Broad City and Insecure.)

Insecure does not have the polish, avariciousness, or puns of Sex and the City (though the men are very cute and it does over-rely on more elaborate versions of “bitch, please” as a punchline), but it is the first show I have seen in a while that does not run screaming from a detailed kind of boy talk, a cataloging of bad dates, and a direct look at the fear of getting older, alone. The whole notion of the “strong” woman has been successfully destabilized by a host of difficult, antiheroic women, but it is still surprising to watch Molly burst into tears at her office when she learns that her very nice (Asian) colleague is engaged (to a black man). Is this retrograde, cliché, or honest—or all of the above? The specific pressures on educated black women may have inspired Rae to take on this material, but Molly and Issa’s worries feel pretty universal.

Dating apps regularly get name-checked in contemporary comedies, but Insecure captures how exhausting they are, precisely because they are so limitless: There’s always another, better app, with another, better guy to hold out for. Molly’s dating is compulsive and disappointing. She is a catch, but she’s also controlling. She meets a guy she likes, who likes her and her bossy ways, but he didn’t go to college, and she thinks she can do better—she can get a date with a college graduate at the swipe of her finger anyway. Molly’s troubles reminded me of an episode of Joe Swanberg’s new Netflix series Easy, an anthology series about relationships, in which Malin Akerman and Orlando Bloom play a happily married couple who learn about Tinder and use it to have a threesome. The vision there is idiotic tech-utopiast: Look what you can find now! Anything you want! (Which may be true if you look like Malin Akerman or Orlando Bloom.) But dating on the internet is like dating off of it: complicated. “You have to [date] a lot of frogs to get a better frog,” as Molly says. Insecure is a show that’s candid enough to show women looking for, among other things, that better frog.