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What Is Friendship For? ‘Insecure’ Is Still Trying to Find Out.

Can Issa and Molly be the best version of themselves and still be best friends? The Season 4 premiere of Issa Rae’s hit HBO show starts with that essential question.

HBO/Ringer illustration
Spoiler warning

“Honestly,” Issa (Issa Rae) says into the telephone while sitting on her couch at the beginning of the Season 4 premiere of Insecure. It’s well past midnight in her dimly lit L.A. apartment; we’ve just seen a red neon sign reading “Good Vibes Only,” as another one of Insecure’s “show inside the show” sitcoms plays in the background. Issa is about to get real, maybe for the first time, about the show’s most important relationship. “I don’t fuck with Molly anymore.”

Followers of HBO’s Insecure, created, written, produced by Rae, have been waiting for this moment. Issa and Molly (Yvonne Orji) have been teetering—sometimes amicably, sometimes uncomfortably—between friends and foes for much of the show’s three seasons. Their relationship is one of the main thrusts of Insecure, a beautifully shot, deliciously sound-designed show centered on the friendship of Issa and Molly, two black women in their 30s living in L.A. Insecure is, by and large, for black women and by black women; its return is a refreshing addition to my weekly viewing.

The tension between Issa and Molly has always been inescapable. In Season 1, Issa used a private moment Molly shared with her in confidence and turned it into a freestyle rap in front of strangers to score points with an ex-flame. In Season 2, Molly ignored Issa’s advice against gallivanting around town with a married man. Season 3 appeared to be the low point of their troubled friendship. Molly, continuously unsupportive of Issa’s dreams, turned away Issa’s love interest, Nathan, on Issa’s birthday, resulting in a spirited back-and-forth.

The first episode of Season 4, “Lowkey Feelin’ Myself,” brings us back to Issa’s couch. Back to Issa hustling, just trying to make it. She and Molly have started “self-care Sundays,” another doomed-to-fail idea to salvage their relationship. They rip a few pulls of a tightly rolled blunt while sitting next to each other on yoga mats. “Namaste, bitch! Light it up!” Molly says. Their jovial conversation hints at recent events in L.A., as well as the city’s changing character. Issa wears a “Slauson” shirt in honor of the late rapper Nipsey Hussle, who was killed in South L.A. last year. Molly explains how a white lady tried to cut her in her grocery store. “I coulda cussed her oat-milk-drinkin’ ass out! But I said, ‘Nope.’ That emotion does not serve me.”

It feels like a whole new world for Insecure. Molly has settled into her new job, where she had been trying, unsuccessfully, to be a boss. Issa is a property manager, which has come with the perk of a lovely new apartment. They reminisce on how far they’ve come as their blunts almost burn their yoga mats. Issa is organizing a block party to celebrate black life and culture in Inglewood, the L.A. neighborhood dramatically changed by gentrification. She enlists the help of Condola (Christina Elmore), whom she met through her friend Tiffany (Amanda Seales). Condola is a chic, elegant, high-performing public relations professional—the kind of woman Issa has always seen herself as becoming. They strike up a friendship as they plan a mixer to gain sponsors for Issa’s block party.

Still, even as Issa makes encouraging moves professionally, she and Molly are on different planes. Molly is dating Andrew (Alexander Hodge), who cooled on her last season because Molly still doesn’t know how to act, forreal forreal. Issa, meanwhile, is sleeping with some random dude that works as a TSA agent at LAX. (I’m hoping it’s LAX. I don’t want her to be ensconced in a fling with a man who’s confiscating hand sanitizer in black Air Force 1s in Burbank.) They seem to have made some amends. Molly is understanding when Issa expresses her anxiety about not having the right clothes or connections to impress sponsors at her mixer. It’s as though they’ve gone to therapy for the first time in 30 episodes (with the exception of the time Molly ran away from the first therapist she had ever seen in Season 2).



Shit starts poppin’ off.

In a meeting with Condola and Tiffany, Issa finds out that Condola’s new man is Issa’s ex-boyfriend Lawrence (Jay Ellis). The revelation was shocking at first, and then it felt tired. Season 3 of Insecure felt waterlogged—thrilling moments captured by gorgeous frames, but beset by the show’s insistence on fulfilling Lawrence’s character development at the expense of its robust, black female characters. It’s a frustrating dynamic that’s plagued Insecure since its inception. Why does a show about Molly and Issa’s friendship always find its way back to old tropes and silly subplots? How is Lawrence, this troubled, trash-ass man, still around and siphoning away the power of black womanhood that is the show’s appeal? Insecure often, albeit crudely at times, points to feminism as a narrative arc; yet somehow, Lawrence continues to come back and diminish its effect. It’d be one thing if Lawrence and Issa’s relationship resembled Kyle and Maxine in Living Single, or even Nicki Parker and professor Oglevee in The Parkers. Lawrence’s presence in Issa’s life has served only to ruin her chances at happiness, her friendships, and the show’s plot lines. When Issa finds out that Lawrence and Condola are dating, and that they met at Tiffany’s baby shower, there’s an awkward pattern of silences in Condola’s office.

“This is, um …” Condola trails off.

“Sooooo dope!” Issa mumbles. “Of course y’all are together! You’re dope! He’s dope! Y’all dope! I’m dope, too!”

“L.A. is just so small,” Condola says, averting her eyes from Issa.

“So small!” Issa replies. “Where are all the good men at?! Where yo exes? Lemme run up on them like you running up on mine!”

They both laugh, though it’s clear the tension isn’t going away anytime soon. Issa tries to call Molly after her encounter with Condola, but Molly doesn’t answer. Issa starts daydreaming about Condola and Lawrence having sex at Tiffany’s baby shower. It’s Insecure at its delightfully deranged best. Issa and Condola’s exchange sets off a cascading series of events: Condola disinvites Lawrence from the mixer after they argue over her friendship with Issa. Molly brings Andrew, but he tells her they’re not exclusively dating on the way to the event, which sends Molly off the deep end. Condola and Issa become so entangled in their newly revealed connection to Lawrence that Issa nearly fumbles an opportunity to impress a big sponsor. The warm feelings start to evaporate. Molly makes fun of Issa for bringing “TSA bae” to her mixer. Issa makes light of Molly’s problems with Andrew because she’s busy chasing her own dreams, which, in typical fashion, Molly misinterprets as Issa being a bad friend. She sends Andrew home while Issa impresses the sponsors with a speech about taking back Inglewood.

At the end of the night, Molly talks to Issa about her feelings. Issa gives some spirited advice, but Molly tells her to “stop frontin’,” and an argument ensues. Molly feels a type of way that Issa didn’t tell her about Condola, and scoffs at the idea that Condola and Issa can be friends with Lawrence in the middle. “You know your life doesn’t have to be this messy, right?” Molly says. “Sometimes, I think you like that shit.” Issa’s face doesn’t seem to see it that way. There’s tension in the air. Tension from seasons past. Anger from former decisions. Angst about how to recover from yet another setback in which one friend sees success and the other sees only failure.

It seems like all the good vibes are finally gone. Perhaps for real this time.

Best Comedic Relief

Kelli (Natasha Rothwell). In the Season 4 premiere, Kelli tries to sleep with an older white man for the sake of Issa’s success. “You know what they say: The stronger the libation, the bigger the donation! You see Spencer over there? He offered me a cold five figures for one night of passion. Now, I’ll take one for the team, just say the word.”

“I’ll never say the word,” Issa responds.

Never Change, Issa

The sex scene between Issa and her new man, TSA bae, is absolutely perfect. TSA bae calls Issa a Rubik’s Cube because they can’t figure out the right position—until they revert to a tried-and-true classic. “That missionary really be hittin’ tho,” he says. “I mean,” Issa replies, “church is always the answer.” As he’s getting dressed, TSA bae notices Issa has a fan in her room. “You sweat on me a lot last time, so ...” Issa says. “Well,” he responds. “Welcome to a full-size nigga,” and then gives her a gift including Hennessy and a medicine vial of kush. “Don’t ever change,” Issa says.

Points for Product Placement

When Issa and Molly go shopping for the mixer, Issa keeps returning clothes that “don’t fit” while exchanging them for new clothes to impress people. She also tells Molly that next to the “real brands” that are coming to the mixer, she got “Wayne from Popeyes” to come as well. “I mean, girl,” Molly says. “Everybody love that chicken from Popeyes.” The writing team better have gotten a bonus for that ad placement.

Never Forget

Lawrence is still the corniest dude in the world. That’s it. That’s the take.

Disclosure: HBO is an initial investor in The Ringer.