I would forgive you if you didn’t really remember much of what happened in Insecure in its third season, which aired in the late summer of 2018. That feels like a lifetime ago! A reminder, from my review:
Think about how Dro says to Molly after the fight in the Lyft involving rider Nathan “with the face!” (Kendrick Simpson) that “You and Issa do the fucking most,” and of the pair of young women that Molly and Issa picked up who reminded them so much of their prior selves. Molly and Issa aren’t those girls anymore, but they’re not the people they want to be quite yet, either. That space in between is what Insecure is so good at exploring, and season three is stronger than ever.
But by the end of the third season, with finale “Ghost-Like,” some storylines felt like they were treading water. Molly’s (Yvonne Orji) frustrations with her workplace and her increasing emotional distance from her family. Issa’s (Issa Rae) indecision with her next career move and her still messy romantic entanglements. Lawrence (Jay Ellis), being Lawrence. Why are you still around, buddy?! I am thankful, then, that this fourth season of Insecure finally pivots away from some of these questions and dives into something deeper and uglier: a friend breakup between Molly and Issa that is remarkably recognizable and fairly devastating. Fourth season premiere “Lowkey Feelin’ Myself” doesn’t beat around the bush, making clear from the opening scene that Issa doesn’t really fuck with Molly anymore. What could have happened to cause their division? And what do we know, from seeing these best friends push and pull at each other over the past three seasons, that would make this fissure not really super surprising?
I’ve seen the first five episodes of this season, and so I won’t spoil too much here, but I will say that I’m satisfied with how the show handles this separation. Each of these episodes moves us simultaneously one month closer to Issa’s block party and one month deeper into Issa’s and Molly’s increasingly fraught relationship, and I am assuming, given what happens in fifth episode “Lowkey Movin’ On,” that we then move forward in time rather than backward. That structure for this season is a nice change of pace for Insecure, which otherwise is a little conservative in these first five episodes. Issa’s mirror raps, which were so ubiquitous in previous seasons, only show up a few times here, and during one of them, her reflection taps out: “I’m sorry. I can’t. Not today,” her duplicate admits. There’s a sense of weariness running through these episodes that I appreciated—a frustration with your job, with your family, with your friends. That’s not to say that these episodes are about straightforward struggle, necessary, but about hitting your 30s and really asking yourself: What am I doing here? Who am I surrounding myself with? Why?
When you consider those questions for Issa and Molly, the answers are a mixed bag. In “Lowkey Feelin’ Myself,” Issa is still working on her planned block party, which she envisions as an opportunity to highlight black-owned and black-operated businesses in her rapidly gentrifying neighborhood. Although she’s also the property manager of her apartment community, we never see her work on that job; she’s more prickly and combative with her residents than anything else. (Issa’s tenant Trina, played by Elle Lorraine, is a recurring thorn in her side, but she’s not wrong that Issa is pretty bad at this gig!)
Instead, all Issa’s efforts and energy are going to the block party, which she is planning with the highly efficient and well-connected Condola (Christina Elmore). In typical Issa fashion, though, once she learns that Condola and Issa’s ex Lawrence are dating, it trips her up. A mixer to rub elbows with potential sponsors and vendors for her block party doesn’t go entirely as Issa planned, especially not after she imagines Condola and Lawrence going at it, during which Condola brags to Issa about her ability to manage her budget without constantly needing to exchange clothing purchases all the time. But Issa is committed to the block party, and it’s clear that she’s more passionate about this than she possibly ever was during her nonprofit days at We Got Y’all.
Does Molly see that, though? Not entirely. She doesn’t quite understand how Issa and Condola have connected so well, especially once Issa knows that Condola is dating Lawrence, and it’s clear that she feels a little left out of their dynamic. Plus, Molly has her own problems: She’s no longer seeing the therapist of seasons past. She’s cut Dro (Sarunas J. Jackson) out of her life, but she’s still not on entirely good terms with her father, whom she learned cheated on her mother. At work, she’s still struggling to make connections and find her place. And although she’s still having solid sex with “Asian bae” Andrew (the very hot Alexander Hodge), she wants something deeper in their relationship—and is thrown when she learns he’s dating other people.
“Lowkey Feelin’ Myself” effectively plants two seeds here that we’ll watch grow over the course of the season, and both are rooted in the complacency and resentment that can seep into friendships over time. For Molly, it’s being Issa’s financial resource for so long—she’s seen Issa flounder in her career choices, and so she’s dismissive of the block party. She doesn’t think Issa can pull it off, and she doesn’t trust Condola. Think of how fiercely loyal Molly can be, and how much it takes for her to let someone in. She doesn’t understand why this new Issa seems to be replacing Molly with Condola as her functional friend, and it’s understandable why she would feel slighted. On Issa’s part, Molly’s friction with Andrew feels familiar, too, but in a different way. Molly has never been in a real relationship—she’s always screwed around, whether Issa, Molly, Tiffany (Amanda Seales), and Kelli (Natasha Rothwell) were on a girls’ trip together, or with the aforementioned Dro, even when he was married. And now she’s ready to give her heart to Andrew, but perhaps she’s assuming too much—she might be in a place he hasn’t reached yet. From Issa’s perspective, it’s Molly again overcomplicating a situation, setting herself up for disappointment. As viewers, we can sense that each of these women is actually trying to break out of their own self-destructive patterns—but as each other’s best friends, they’re too close to see it. There’s too much history there, and it’s getting in the way of the future.
This is the story I’m interested in: When do the people we know stop knowing us? And this is where I must say, again—because I’m pretty sure I said it last season, too—that I don’t understand why Lawrence still has a role in this narrative anymore. Every time he pops up in these first five episodes, I was surprised because he’s not a requirement. We get a few stories entirely from his perspective this season, and it’s bizarre to me. Yes, he is still in the same friend group as Issa—his best friend Derek (Wade Allain-Marcus) is married to the very pregnant Tiffany. But does that warrant this much screen time given to Lawrence, when characters like Tiffany and Kelli feel like they have even less to do this season? Meanwhile, I’m grateful for an increased presence for Issa’s brother Ahmal (Jean Elie)—the siblings spend Thanksgiving together in an episode that does a lot to flesh out their relationship—and for the still-sparseness of Lawrence and Derek’s fast-talking, womanizing friend Chad (Neil Brown Jr.). He remains amusingly offensive and egotistical, and his appearances are always some of the funniest moments in each episode; a rant he gives in a later episode about Bradley Cooper’s career is perfect because it’s so confident but also so out of touch.
Ultimately, this fourth season of Insecure seems like it’s structured around something Lawrence says: “I wish there wasn’t always one piece missing.” It’s irritating that the show gives Lawrence what is basically the thesis statement for this statement, but I deeply relate to this complaint—that it feels like what you have a handle on in your life is ever-shifting. That you never have every single thing under control. That uncertainty can transform you—can change how you treat yourself, how you treat your colleagues, how you treat your family, how you treat your friends. It certainly changes how Issa and Molly treat each other, and I’m pleased that Insecure is going in that direction this season rather than yet another romantic retread.
Some stray thoughts:
+ Ahmal says to Issa at one point, “You ain’t gotta do something just because they say you’re supposed to,” and please cross-stitch that for me so I can hang it up in my office, thanks.
+ Second episode “Lowkey Distant” is set during Halloween, and Issa’s, Molly’s, Tiffany’s, and Kelli’s costumes are perfect. They are so thoughtful and reflective of each character; I was impressed. And when Tiffany buys Halloween “treats” that are made with broccoli extract? Also on brand for her—as is Kelli throwing those items across the room.
+ Kelli isn’t around much this season, but in one scene she has an argument with Ahmal that continues their long-gestating beef, and it’s the most I laughed during all five episodes I watched.
+ I lean toward thinking that Issa’s hookups with “TSA bae” Calvin (Reggie Conquest) are playing his body for laughs? Anyone else think that first sex scene focused more on the size of his butt than anything else about him? There’s a scene in another episode that furthers my theory on this, and I kind of hate it.
+ This season’s show-within-the-show is Looking for LaToya, a true crime miniseries following the disappearance of a black woman and featuring cameos from Ray J, Porsha Williams from The Real Housewives of Atlanta, and Terri J. Vaughn, from various sitcoms, including The Steve Harvey Show. The recurring gag here is that the white cops assigned to find LaToya keep thinking they’re looking for a lost Toyota, and this is your reminder that you should be watching HBO’s Atlanta’s Missing and Murdered: The Lost Children.
+ Vince Staples appears in a later episode, and if you don’t follow him on Twitter, you should. He deleted this tweet, but it’s one of the BEST OF ALL TIME:
+ I know it’s often silly to look for realism in a TV show, but I remain amazed by everyone’s apartments. Issa’s hardwood floors? Lawrence’s built-in bookcases? Molly’s kitchen? Goddammit! Come on, man!
+ For everyone wondering why Insecure wasn’t prefacing every sex scene with someone putting a condom on, there is a very gross fuck you to those viewers in the episode “Lowkey Distant.” Get ready.
Insecure started its fourth season on HBO on Sunday, April 12, 2020.
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