Sometimes, the same benefit of someone knowing you for so long is the same disadvantage that comes with an enduring friendship. For Issa (Issa Rae) and Molly (Yvonne Orji), who have been best friends since their college days at Stanford, all the things that they once relished about their friendship–i.e. talking about their usual fixed issues with men–are now the things that appear to be tearing them apart at the seams throughout season four. We know from the get-go that the falling out is impending as the first episode, “Lowkey Feelin’ Myself,” opens with Issa talking to her ex, Nathan (Kendrick Sampson), and explaining bluntly, “Honestly, I don’t fuck with Molly no more.”
So it is that we return to three months before the block party Issa has been planning with the help of her new friend, Condola (Christina Elmore)–soon to warrant the nickname “My Condola-ences” when viewers see the outcome she wreaks–who also just so happens to, unbeknownst to Issa, be dating Lawrence (Jay Ellis), her ex that she dated for five years–their breakup occurring not that long ago. Of course, the pieces of this puzzle quickly come together when Tiffany (Amanda Seales) stops by their office and it comes up that Condola met her new man at Tiffany’s baby shower. Considering the shortage of possible men there, it doesn’t take long for Issa to realize it’s Lawrence, at which time Tiffany is the one to tell Condola he dated Issa. Suddenly, their new friendship is made incredibly awkward at a time when Issa needs her the most for planning the block party.
In the meantime, Molly has been getting closer to her new boo, Andrew (Alexander Hodge), cementing the chasm between her and Issa, who seems all too ready to call her out for her usual self-sabotaging behavior when it comes to driving people away, at one point remarking of her complaints, “He dicks you down, makes you laugh–what’s the problem?” Issa isn’t wrong, of course. With Molly, it is always something. Some flaw to nitpick at or overanalyze to the nth degree until it doesn’t even exist anymore. Issa is becoming less amenable to tolerating this at just the moment when Andrew is stepping in to take over that burden, ergo making it easier for Molly to let go of working at their friendship, allowing the distance between them to thrive as she leans into Andrew more for emotional support, and Issa does the same with Condola now that they’ve gotten over the hurdle of acknowledging the Lawrence thing. Except now, Lawrence is the one who’s uncomfortable–but who cares about his comfort anyway? Except, foolishly, Issa. And while she might have the lowkey fling of Calvin a.k.a. “TSA Bae” (Reggie Conquest) to keep her sexually satisfied, her emotional connection seems destined to find itself back to, once again, Lawrence. Though, granted, her friendship with Nathan begins to thrive as well, and sympathy arises for his ghosting actions in season three when we’re given the real reason behind it.
With the rift between Issa and Molly solidifying around Thanksgiving, in the episode “Lowkey Thankful,” the former decides to opt out of showing up to Molly’s house for pie despite promising she would, suddenly inspired by her brother’s words to not do anything she doesn’t want to. Considering her stress level with regard to planning the block party, it’s only natural that she should have less emotional energy to give than usual to the highly demanding Molly. What’s worse, when her headliner for the party, Schoolboy Q, drops out, Issa makes the mistake of assuming Molly will show up for her to ask Andrew, who works for Live Nation, to get in contact with the rep for an artist she’s interested in replacing him with. Molly, driving another wedge into their relationship, refuses to help, saying she doesn’t want to jeopardize what she has with Andrew by asking for a favor.
The tensions between Issa and Molly are nothing new, with one of the peaks coming at the end of season one, when Molly exposes Issa for some fuckery with Lawrence to their other friends, Tiffany and Kelli (Natasha Rothwell). In fact, Molly has long been coming for Issa in terms of shading her for being “messy” and a “user.” It is this latter accusation that leads Issa to force herself to perform a series of favors for random strangers that all end up backfiring in some way in “Lowkey Done.” Feeling adrift after the high of her block party’s success (minus the part where a lot of white people showed up, negating Issa’s mission behind the event and the part where it ended in a major blowout with Molly that was interrupted by the panicked announcement that someone had a gun), Issa still isn’t desperate enough to feel like she should be the one to apologize to her so-called best friend. Even when she sees her at the Ethiopian restaurant they both like as she’s about to pick up a takeout order, she decides the food ain’t worth it and flees, thinking Molly hasn’t noticed her, which, of course she has.
In the post-public fight episodes, the two start to get closer to the men in their lives as both are subconsciously seeking to replace the other with these romantic distractions that can serve as no substitute for the deeper intimacy of platonic love. Yet the more they try to tell themselves they’re doing better without one another, the clearer it becomes that both thrive on what is ultimately the toxicity of the friendship, each getting off on the ability to be the most negative versions of themselves with the other. “Maybe who you are now and who I am now don’t fit together anymore,” Molly coldly says at one point toward the end of the season. And yet, the second neither of them has a project or a romantic prospect to make them believe that they can do better than their decade-long friendship, they come running back for more of the undercutting hostility that always seems to flourish inevitably between them.
And yet, the rare friendship that lasts a long time becomes like the dynamic between an old married couple: one can’t recognize any longer if they’re still in the relationship because they genuinely care about the person or because they’ve gone so many years with that person in their life that they can no longer envision an existence without them that wouldn’t entail constantly feeling a phantom limb as a result of their extraction. Even if Issa and Molly become more “zen” in season five (as they tried to this season with Self-Care Sunday), the underlying root of their affinity has long stemmed from a place of letting their negativity feed off the other’s–Molly being the most guilty of this crime, which is precisely why Issa calls her out for being inherently miserable and not actually wanting to be happy. In turn, she seems to not want Issa to be either, because it places into question the entire validity and value of their friendship.
Issa, unfortunately, and as so many in her position, can’t bring herself to let go of this energy in her life because of that trick of the mind called sentimentality. This, too, applies to a similar narrative in 2001’s Me Without You, in which one of the lead characters, Holly (Michelle Williams), has to finally make the conclusive decision to cut the cord with her toxic “bestie,” Marina (Anna Friel), after over ten years of putting up with her treacherous bullshit for the sake of, what, nostalgia? In the end, Insecure broaches an all too common fact of life–that friends outgrow one another–but cannot run all the way with it, preferring to showcase the theme that platonic friendship–no matter how toxic–is still more enduring than any romance.
