Insecure’s Nuanced Take on Singleness

This post contains light spoilers through Season 2, Episode 1 of Insecure.

Issa and Lawrence are sitting across from each other in a dimly lit restaurant. “You know, I get why you did what you did now,” he tells her. Issa nods. “And it hurts,” Lawrence continues. “But hopefully we can move past it.”

Issa smiles. It’s exactly, it seems, what she’d been wanting to hear. And then: “What?” she says.

“I said, are you originally from here?”

With that, Issa (Issa Rae) snaps out of her reverie. She is not, it turns out, sharing a romantic meal with Lawrence (Jay Ellis), the ex-boyfriend she cheated on, and the ex-boyfriend who is still sort of in her life, and the ex-boyfriend she still wants back. Issa is instead, in the Sunday premiere of the second season of Insecure, sitting at that table with a total stranger: a guy she met through Tinder (or maybe Hinge, or maybe Bumble, or maybe one of the other services that has transformed Issa’s phone into a buzzing catalog of suitors who are at once omnipresent and extremely far away). This particular guy is anonymous, to the viewer. And he will remain that way. The real point of the scene is not who he is, but who he is not.

Lawrence, here but not-there: It’s the kind of fake-out Insecure is so consummately skilled at executing—the kind that the show’s Season 1 finale deployed with such gut-wrenching precision (Lawrence! In that other apartment, and in that other bed!). Issa’s date-dream, which serves as the cold open to Sunday’s episode of Insecure, also serves as jarring evidence of her new situation: Issa, technically, is now single. She’s been that way for months. And yet, in the more immediate sense, she’s not fully single at all. She still wants Lawrence. She’s dating, sure, but her heart isn’t in it.

“I don’t want to be here, but my ex won’t take me back,” Issa raps in an aside during several more anonymous dates with several more anonymous Tindermen—a composite set at different restaurants that are dimly lit and romantic in feel and, effectively, the same place. “So my broken ass is here, small-talking over apps.”

Insecure, overall, is a show that is deeply interested in the here—in the way locations, and circumstances in general, shape people’s lives. The tension that results, one place chafing against another, is where the show’s title itself comes from, Rae once explained—“we wanted to kind of paint that this character is in between two worlds and is just in a constant state of discomfort”—and it’s one that manifests not only in Insecure’s storylines, but also in its production values. That’s one of the elements that make Insecure such a stand-out series, one of the best TV shows in an environment crowded with great ones: the attention it pays to geography, and architecture, and interior design, and the physical spaces its characters inhabit. Many of the show’s scenes begin with quick-cut montages that serve not only to locate their action within particular settings, but also to emphasize the constraints of location itself: Whatever action is about to occur will to some extent be shaped by the spot where the scene is set.

In its Season 2 premiere, Insecure extends that idea: Singleness here, too, becomes a space that characters live in. “Single” is, Insecure is suggesting, not merely a status, in that reductive, drop-down-menu way that Facebook—another omnipresent space in the show—conceives it. “Single” is instead a space to be navigated and negotiated. It carries certain expectations. It makes certain demands.

That’s already been the case for Molly (Yvonne Orji), Issa’s best friend, who began Season 1 reeling from the engagement of a coworker—and who spent much of the rest of the season’s episodes worrying, in various ways, that coupledom might not happen for her. But now, after her breakup with Lawrence, Issa has joined Molly in that space—and her singleness has become for the moment, it seems, the salient fact of Issa’s life. It takes over her conversations with Molly. It leads her to throw a party, and to ask each guest to bring a plus-one. It crosses over into her efforts to bring We Got Y’All, the educational nonprofit she works for, to a new school that seems to have no interest in its services. (“Sometimes you just have to know when to give up,” Frieda (Lisa Joyce), Issa’s co-worker, says; she’s talking about the school, but the show allows the observation to adopt a kind of doubleness—as a commentary about Issa’s relationship.)

And: Issa’s newly single status becomes a matter of physical space, as well. Issa, still, sleeps on a single pillow, on her half of the bed she used to share with Lawrence. She sits on the couch she and Lawrence bought together—the piece of furniture that once symbolized the renewal of their relationship. She keeps dating apps constantly fired up on her phone, ensuring that men flexing and ab-revealing and smiling in bathroom mirrors runs like a visual refrain as she watches TV, gets ready for bed, and lives her life—even though she rejects almost all of them. And when Issa does swipe right, she returns, again and again, to that dimly lit, composite restaurant: Different outfits, different men, but otherwise—place-wise—the same. She’s meeting new guys, but she’s not getting to know them; she is going on dates, but she is not really dating. She’s there, but she’s not really there.

It’s a typically nuanced take for Insecure, a show that rejects easy tropes and revels, instead, in complexity. While many of its fellow comedies treat newfound singleness as a matter of tragedy and melodrama (tears, couches, tubs of ice cream) or of insistent liberation (clubs, hookups, pep talks from friends), Insecure is offering something much more subtle, and much more realistic: singleness treated as a simple fact of life. And singleness that is, in its own way, unsure of itself and insecure. Is it good for Issa, or bad, that she’s single? How long will she stay that way? How will it change her? And should Lawrence take her back?

Lawrence, too, as Season 2 begins, is trying his singleness on for size. He’s dating Tasha (Dominique Perry), the bubbly bank teller he chose over Issa at the end of Season 1. But he is only dating Tasha. As his friend Chad (Neil Brown Jr.) diagnoses the situation: “Roll in on Fridays, smash all weekend, bounce on Sunday.” Chad adds, approvingly: “It’s low-maintenance, efficient, all upside.”

It’s not all upside, though—as becomes very clear at the twist-y end of the show’s Sunday premiere. Lawrence, too, is slightly uncomfortable in his singleness. He spends the episode sleeping on an air mattress in Chad’s living room, unable to commit to renting a new place on his own—a new place without Issa in it. Which is to say that, in many ways, the beginning of Season 2 of Insecure finds both Issa and Lawrence in the same place the beginning of Season 1 did: They are, both together and separately, caught in a rut. For Issa, dating is too much work. (“I’ve got to be cute, and careful, and witty, and charming,” Issa tells Molly. “It’s a lot.”) And for Lawrence, dating is almost too easy. (“We’re both having fun,” he tells Chad. “No pressure.”) The question the premiere has set up—the question that is a matter of geography as much as it’s a matter of romance—is whether the two will be able, once again, to meet in the middle.

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