Insecure fans have been dealing with Issa Dee’s drama for the past few years. We started season one watching her live an awkward and unfulfilled life—uncertain about love, uncertain about her job, and constantly unsure of her life choices. The one constant had always been her friendships, especially with Molly (Yvonne Orji). Their sisterhood was an assuring underlying theme. There was comfort in knowing that no matter how much Issa (Issa Rae) frustrated us with her sometimes questionable actions, she could always turn to Molly.
But then season four premiered in April, and it became clear that their friendship is falling apart. Prior to season four, Issa’s most defining fallout had been her breakup with Lawrence. It had been fodder for online after-show arguments and discussions. These days, the show is going in uncharted territory by tackling a breakup that might be one of the hardest types of breaksups for anyone to deal with—the separation from a friend. Boyfriends come and go, but Molly and Issa were supposed to ride or die forever, right? That is the question we’re examining this season.
Actually, that is one of the questions we’re examining this season. There are so many more questions now that we are seeing a different dynamic play out between Issa and Molly. Were they ever really friends? Did they hold on to a fraying bond longer than they should have out of comfort or obligation?
Are any of Issa’s friendships actually good for her or are they all just toxic?
As we approach the next episode on Sunday night—an episode where she reunites with Lawrence once again, and we’re collectively anticipating how this will go—we should take a more discerning look at how Issa’s friendships may have affected her life thus far because overanalyzing everything on this show is what we do. It’s what this season has been forcing us to do anyway, so here’s a power ranking of Issa’s most significant friendships in order of impact from least to greatest.
We haven’t seen Frieda (Lisa Joyce) since Issa left We Got Y’all, and that’s a good thing because We Got Y’all wasn’t a good time in Issa’s life due to the constant microaggressions she experienced. Frieda was the only one of Issa’s coworkers who actually tried to get to know her. It was a work relationship that got off to an awkward start and had some bumps along the way—like that time Issa caught Frieda trash-talking about her perceived work ethic with other coworkers. Issa called Frieda out on it, and the conversation was surprisingly productive, but their awkward interactions didn’t stop there. There was also that time when Issa and Frieda were tasked with getting We Got Y’all established at a high school that had a predominantly Latinx student body. The principal expressed some prejudiced views about the Latinx students. Both Issa and Frieda agreed that what he said wasn’t cool, but Frieda insisted that Issa be the one to speak up about it as if to say, “Only the black girl could call out another black person,” when they actually could have worked together. Their dynamic highlighted the complexities of having an intercultural friendship and how such friendship could be beneficial to fostering better understandings among people from different backgrounds. This was one of Issa’s more superficial friendships because it was only beneficial to work survival, but it made her appreciate her core group of friends a lot more. Hopefully moving forward, Issa can make more work-related connections that are about more than mere survival.
9. The Bachelorettes
This friendship turned out to be a bust. It started out with so much promise, especially during a time on the show when we were rooting for Issa to get new friends. Issa met Kinsey, Dina, and Rahel (Emana Rachelle, Kyla Pratt, and Mykal Monroe)—who were celebrating Dina’s impending nuptials—right when Issa was feeling the worst about the fracturing of her bond with Molly. They met at a sip-and-paint and seemed to click. The women even got personal with Issa, explaining to her that when it comes to their friendship, they’ve been through it all but still manage to have each other’s backs. You could see Issa admiring what they had, even as they explained some of the missteps they’ve experienced together. But it turned out they were using her for a game they created for their bachelorette party shenanigans. Issa finds a list of game challenges that include befriending a stranger and dining and dashing—double points if they can do both at once. They invited Issa to have drinks and sushi with them, and then ditched her at the restaurant. Issa’s brush with this group of pseudo-friends was fleeting, and it would have been nice to see her get revenge, but the encounter at least provided her a brief reprieve from her friendship heartache. Bottom line: Issa will be okay if she decides to hang out with new people.
Issa and Condola (Christina Elmore) could have been great, but their budding friendship took a turn for akwardville after they discovered they had Lawrence in common. They were initially brought together by their mutual friend, Tiffany, who figured Condola had the perfect skill set to help Issa with her block party. They worked together in harmony and even seemed to be developing a promising bond until they realized that Lawrence also met Condola through Tiffany and they started dating. Issa and Condola pretended to be cool about it, but when things went south between Condola and Lawrence, Condola took it out on Issa by ghosting her during the block-party planning. This one is extra disappointing because they had great chemistry. But at least Condola revealed who she was before things got too deep. Uncomfortable friendships aren’t worth the headache.
Daniel (Y’lan Noel) was Issa’s one that got away turned never should be. We haven’t seen him on the show in a while, but in Insecure‘s early days, he kept popping back into her life just in time to create chaos. Issa cheated on Lawrence with Daniel, which led to her big breakup with Lawrence. The tension between Issa and Daniel was intense as they fell into a friends-with-benefits routine, and they kept doing this frustrating back and forth about whether they would be together or not until Issa finally figured out that they wouldn’t be a good fit. A friendship like this would never work if underlying sexual tension constantly complicated things. Still, Daniel provided Issa with an important lesson about the direction of her life: Perhaps Lawrence wasn’t the one after all. She was afraid of being single, and Daniel just helped her speed up the process.
We first met and swooned over the L.A. transplant after he defended Issa’s honor in an Uber when another passenger got disrespectful with her. Issa and Nathan (Kendrick Sampson) kept in touch after that wild ride and had a great time as Issa showed him Los Angeles. Life after Lawrence seemed promising, and we liked Nathan a lot, but then we didn’t know what to make of him after he ghosted. We were ready to hate him for Issa, but it turned out that he struggled with his mental health and was overwhelmed with life, so it was best for him to not pursue a romantic relationship. Issa respected that and gave him the space he needed. That allowed them to get back to being friends without complication.Their relationship is in a good space as Issa respects Nathan’s boundaries.
Lawerence (Jay Ellis) and Issa still have feelings for each other and it’s exhausting. They’re trying to be friends and keep exchanging basic but loaded pleasantries, but things are still awkward between them. This is not how a true friendship should be. Their relationship can be best summed up by Musiq Soulchild’s “Mary Go Round.” Perhaps they will get back together, perhaps not. That has been a burning quandary since their breakup at the end of season one, and on Sunday night’s episode, we revisit this. The trailer shows them hanging out again, and you just never know what this means. The #LawrenceHive and #TeamIssa will forever be divided on the issue of whether they should reunite or not, but one thing everyone can agree upon is that they need to be direct with each other and stop communicating like they’re in high school. It’s a lesson they haven’t seemed to learn yet.
Tiffany (Amanda Seales) and Issa are polar opposites; you often wonder why they’re even friends at all. Tiffany is constantly putting up appearances as if she has the perfect life while Issa doesn’t hide the fact that her life is a mess. However, they see things in each other that they do admire. As perfect as Tiffany tries to appear, she wants to be free to be a mess sometimes, while Issa wonders what it would be like to get her life together. Tiffany also delivers moments of brutal honesty that Issa needs. It’s often harsh, shady even, but Issa sometimes lets life happen to her instead of planning accordingly. Tiffany keeps her in check.
We don’t quite know how this core group of friends met, but it’s likely that it happened in college and that Kelli (Natasha Rothwell) is the force who brought them all together. Kelli is the one person in their group who is actually secure, even when it means being a mess. She is loud and unapologetic, but is content with her work and dating life, and with being a mess when she chooses to be—even if it means faking a London accent to a romantic prospect. Kelli has been the constant voice in Issa’s ear this season, telling her to work things out with Molly. Kelli has also helped Issa with other life stuff, like getting her bills together and figuring out how to get a new apartment. We don’t see Kelli and Issa’s dynamic play out as much as that of Issa and Molly, but Kelli has proven to be more of a rock-solid friend than Tiffany and Molly. Kelli isn’t without judgment, but she’s upfront with it, it comes from a place of love, it’s usually hilarious, and it’s definitely always true. Kelli is the type of friend that everyone needs. If Issa falls out with everyone else, at least Kelli will (hopefully) still be around.
Their friendship seemed to be the stuff we dream of, but perhaps they’ve only been tolerating each other this entire time. Their underlying mutual annoyance has been present since the “Broken P—y” incident. When the series started, it was established that Molly was a pretentious type A with an amazing career as a high-powered attorney, but no keeper boyfriend. Issa hated her job, hated her (lack of) career, and questioned her romantic relationship with Lawrence. Issa was the friend who didn’t have her life together. This season, Molly still has a job she likes (but doesn’t love) and a promising boyfriend, but she’s still not happy and often sabotages her relationships with her attitude and need to control how people around her behave. Issa doesn’t have a boyfriend and she’s okay with that, but the new career she is carving out for herself has become a source of joy for her, especially with the recent success of the Market Street Block Party. Issa is in a good space and that seems to bother Molly. So now we’re left wondering if Molly was only okay with Issa when she was the underdog in the friend group—when she had someone to look down on. You want them to win, but you also don’t. Should they honor the time they’ve spent together by continuing to make it work or should they cut their losses and a accept that sometimes you just outgrow people?
Expect this new dynamic to spill over into season five.
Ahmal (Jean Elie) can be shady and he’s brutal when it comes to doling out tough love, but he has Issa’s back because he’s her brother. That became clear in episode five this season, when he showed up to the block party. He approached Issa as she stood with her friends, hugged and kissed his sister, hugged and kissed Tiffany (his favorite of Issa’s friends), ignored Kelli (because they have an amusingly antagonistic relationship), and only gave Molly a curt “Hi.” It was a slight that Molly noticed but also a nod to his solidarity with his sister. It has been fun to watch Ahmal and Issa’s relationship play out this season, especially during the Thanksgiving episode. We need more of Issa and Ahmal. He provides the type of support Issa needs in her life and he knows her best. Siblings don’t always get along, but Ahmal’s presence in Issa’s life is vital.