After an ominous opening featuring glimpses of what looks like the aftermath of Issa’s block party, we see Issa (Issa Rae) on the phone telling an unidentified person (in much harsher language) that she and Molly (Yvonne Orji) are on the outs. It’s not the most surprising revelation since the two fought in the Season 3 finale after Molly casually let slip that she had sent Nathan away before he could apologize for ghosting Issa.
“Insecure” cuts the tension by bookending the scene with this season’s show within a show: “Looking for LaToya,” a true-crime program hosted by fictional TV personality Rose Cranberry (Terri J. Vaughn), about the mysterious disappearance of a local 26-year-old woman.
Following Issa’s confession, the audio on her TV gets noticeably louder: “What happened?” Vaughn’s Nancy Grace-esque character asks. “Who is responsible? Did anyone see this coming? Could anyone have stopped it? Is LaToya really missing — or was she murdered?” Aside from murder, these are all relevant questions for those of us watching at home.
But Sunday’s episode, titled “Lowkey Feelin’ Myself,” doesn’t dwell on Molly and Issa’s impending fallout. The premiere flashes back to four months before the block party when the duo were getting together regularly for yoga on what they (and countless Instagram users) have dubbed “Self-care Sunday. As the two catch up over “herbal enhancements,” Issa tells Molly that organizing her apartment has done wonders for her life. “I’m on this forward path. I’m focused,” Issa says. “It’s like no job, no man, no — all this sounds bad, but it’s actually really good.”
Molly, meanwhile, laments that work at her new firm is “draining” her. Issa reminds her that finding her footing will take some time. “We just have to hold each other accountable,” Issa says.
As always, “Self-care Sunday” is over too soon. Issa gets to work, meeting up with Condola — who inspired Issa with her well-attended outdoor screening of “The Last Dragon” in last season’s finale — to discuss a mixer they hope will get investors interested in Issa’s block party.
Over their lunch meeting, Condola gets a text and Issa excitedly asks if it’s “the comeback kid.” Condola smiles as she tells Issa they’re “still going strong” after a month of dating. These two are in the honeymoon phase of their friendship, so it makes sense that Issa has no idea the “comeback kid” is her own ex, Lawrence. But the truth comes out and we don’t even get to the mixer before Issa and Condola’s shared connection is revealed (praise to the “Insecure” writers for not dragging this particularly soapy subplot out).
Issa happens to be visiting Condola at her office while a very pregnant Tiffany is making the rounds. When Tiffany asks about the beautiful red bouquet on Condola’s desk, Issa mentions the yet-to-be-named comeback kid. Condola, completely unaware of the bombshell she’s about to drop, tells Issa that Tiffany’s baby shower brought her and her new boo together, too.
Tiffany pieces it together only a moment before Issa does. When Condola says “his name is Lawrence,” Issa looks as if she might cry. And then she looks at Tiffany, who knew that Condola went on at least one date with Lawrence and never said a word about it. Tiff doesn’t do egg on her face, so she hastily summarizes the potential drama, complete with exaggerated hand gestures: “Issa and Lawrence are exes. They dated, they were a couple, they were together, now they’re not.” Condola and Issa look appropriately uncomfortable.
“It’s fine,” Tiff says as she walks out, leaving the trail of dominoes in her wake. Issa becomes the special brand of chatty that always accompanies her self-consciousness. “So dope,” she says. “Of course y’all are together. You’re dope. He’s dope, y’all dope,” Issa volunteers before sinking back into her chair: “I’m dope, too.”
What happens next is a nod to the show’s “Awkward Black Girl” heart. Issa imagines (montage-style) stumbling across Condola and Lawrence having obnoxious sex at what looks like the early stages of Tiffany’s baby shower. All of Issa’s insecurities come to the forefront: Lawrence tells Condola she’s “so well-connected” and — as Issa realizes she and Condola are wearing the same outfit, tags still on (in Issa’s case, so she can return it later) — he says “I bet you own all your own clothes, don’t you?” “Truuue,” Condola replies, cutting her eyes at Issa. “Oh, Lawrence! Pop the tags.”
By the time the mixer happens, Condola and Lawrence have had their own awkward conversation. Condola learns that Lawrence dated Issa for five years before their breakup. “Wow, that is significant,” Condola says before abruptly canceling their romantic night in, which would have included a “Looking for LaToya” binge (is it just us or is Ray J the perfect person to play LaToya’s boyfriend?)
The mixer is poised to be a hot mess amid the awkwardness between Issa and Condola, who greet each other with an awkward hug and small talk about Condola’s ability to find a parking space. It doesn’t help that Issa takes advantage of her property manager perks and holds the mixer in the courtyard of her apartment complex. Financially, it’s a savvy business move. But awkward moments abound as Issa’s worlds collide: Issa’s casual hookup who works for the Transportation Security Administration (a.k.a. “TSA Bae”) over-enthusiastically embraces his role as event bouncer; Kelli loads up the drinks with alcohol (“The bigger the libations, the bigger the donations,” she tells Issa); Issa’s brother plays Khia’s “My Neck, My Back” — horrifying potential investors — at the request of Trina, one of Issa’s, uh, quirkier tenants.
Molly, meanwhile, shows up after getting into a fight with Andrew, with whom she had been happily getting closer, after he tells her that he’s still seeing other people. Issa is distracted when Molly asks whether it’s a big deal that she and Andrew aren’t exclusive. Molly is judgmental when she finds out Issa is still working with Condola despite the news about Lawrence. Even when Issa manages to pull off a successful event, landing investors and vendors for the block party, Molly is visibly unimpressed.
She stays behind to help Issa clean up but insults her in the process: “You know your life doesn’t have to be this messy, right?” she tells Issa seconds before she texts Andrew, apologizing for “trippin’” and admitting that she likes him more than she realized. Hmmm. Seems like projecting to us!
Meanwhile, Condola returns to Lawrence’s house and makes it clear that she’s still interested in pursuing their relationship. This means it’s only a matter of time before Lawrence and Issa cross paths again. With drama this good, who needs Rose Cranberry? (Just kidding, we all need Rose Cranberry.)