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Insecure's new season forces us to choose: Team Issa or Team Molly?

Illustration for article titled Insecure's new season forces us to choose: Team Issa or Team Molly?
Photo: Merie W. Wallace (HBO)
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It’s been almost a year and a half since Insecure’s season three finale. “Ghost-Like” provided an amazing end to a muddled season. Issa was interviewing for new jobs. Molly was accepting responsibility for her mistakes at work and in relationships, rather than jumping to her defenses. Season three provided huge character shifts for Insecure’s main duo, but that wasn’t always enough to drive an interesting narrative for a show with an oddly or underutilized cast. Kelli, Tiffany, Dro, Lawrence and Daniel all felt like props to drive whatever Twitter debate the writers thought would take off that week rather than fully realized characters.

So, when “Lowkey Feelin’ Myself,” opens on a dark and empty block party and cuts to Issa on her phone, warning someone that she doesn’t really fuck with Molly anymore, it’s immediately intriguing. Did Molly ruin Issa’s block party? Was the separation Issa’s fault? The show then takes us to 4 months before Issa’s call. This makes it clear the season is going to focus on the dissolution of their friendship leading up to the block party so the audience can figure all of that out for themselves. It’s to Insecure’s credit that this tactic works; if the show hadn’t successfully built Molly and Issa’s friendship, this would be one boring opener. Instead, Molly and Issa are both complex, relatable characters and it’ll be interesting to see how the show chooses to spread the blame in their eventual break-up.


Of course, friendship-breakups are never that simple and have more to do with the ways people naturally grow and change, but taking the time to detail the split allows viewers to see who failed to communicate what and when. Also, it’ll probably play out well on social media, a realm Insecure has always enjoyed engaging. And, honestly, #TeamMolly vs. #TeamIssa hashtags feel way more interesting than anything involving Lawrence, Daniel or Nathaniel. Does this mean we’ll finally get a season of Insecure that fully realizes all of its female characters? Maybe. Obviously, a friendship-breakup between Issa and Molly should involve more Tiffany and Kelli and that already makes for a promising season four.

On the other hand, it could mean more Condola. Condola was introduced last season as a romantic interest for Lawrence and collaborator for Issa’s block party. Given this history, their friendship seemed doomed but “Lowkey Feelin’ Myself” shows us they work pretty well together. The episode doesn’t waste time revealing Condola and Lawrence’s relationship, a reveal earlier seasons of Insecure would’ve wasted precious time teasing. Thankfully, Tiffany comes crashing in to bring everything out into the open. Despite being shocked, Condola and Issa both respond to the situation maturely and successfully put on Issa’s fundraiser. Sure, it’s not ideal, but Issa, Lawrence and Condola are all grown enough to deal with this dynamic.

Molly doesn’t see it that way. Or at least she doesn’t want to. Even though Molly praised Condola’s movie event last season and encouraged Issa to ask her for help, she now dismisses the whole situation as messy when Lawrence is involved. Rather than seeing that Issa has matured and can handle this pretty normal, adult situation, she accuses Issa of just loving the messiness. Maybe that’s valid and Molly is trying to hold Issa accountable, but it feels like Molly is just striking back because Andrew ruined her mood. If the situation was as messy as Molly believed, Condola easily could’ve sabotaged the fundraiser or not shown up at all.

Yes, Andrew is still around! Last season ended with Andrew perfectly refusing Molly’s apology for blowing up their situation, but they’ve clearly reconciled. Sort of. They’re going on dates, but haven’t defined the relationship yet as Andrew’s admission that he has a date with someone else shocks Molly. Molly quickly resorts to her old ways and almost ices Andrew out, before sending a text to clear things up when Issa calls her out for making a big deal out of nothing. Andrew lives to see another day.


This moment felt like a letdown for Molly’s character and an easy way to get a point on the board for #TeamIssa. If Molly was reacting to Condola and Issa’s friendship and jealousy was now driving her defensiveness, that would be understandable! And interesting! Sure, they’ve gotten into fights before but their friendship has never been threatened this way as far as viewers know. So why wouldn’t Molly get defensive when she sees how well Issa works with Condola?

But, no, Molly is dismissive of Issa’s event from the start. She still doesn’t care about the block party or take Issa’s goals seriously or seem to care that Condola has taken over Molly’s job of helping Issa “get money from white people.” She even tells Andrew not to expect much from Issa’s event as they drive there. Instead, Andrew is the entire source of her anxiety. Disappointingly, Molly’s emotional growth is still tied to her relationship with a man, just like past seasons.


I like Andrew and would like to see more of Alexander Hodge. He and Yvonne Orji have amazing chemistry and the dynamic between Molly and Andrew is one the character needs. Also, he’s absolutely gorgeous. Still, I hope he isn’t just the next Dro or Jared; only here to teach Molly a lesson on the proper way to “get a man.” Her character deserves to move beyond that dynamic by now. Let’s see Molly in a real relationship. Or let’s just see what else her character wants when she doesn’t want a man or promotion.

And well, that’s kind of a perfect summary of the episode. There’s growth and a lot of promise, but relying on the same old tricks and tropes still keeps Insecure and “Lowkey Feelin’ Myself” from showing viewers something they haven’t seen before.


Oh, and Kelli was there to make jokes.

Stray Observations

  • Issa Rae’s delivery on “Where your exes? Let me run up on them!” and the ensuing laugh were hilarious. Rae has always been a talented actress, but it feels like she’s working on a new level following her many film projects between seasons.
  • I also loved the sex scene with Issa and Calvin, her TSA-bae. Molly’s development is still tied to the men she dates. So, it feels like a great change of pace for Issa to just have a legit, casual fuckbuddy who doesn’t stress her out and treats her nice. I don’t see Calvin inspiring any deep “rapping-to-yourself in the mirror” moments, but he also doesn’t just seem like a punchline.
  • That being said, the moment that stole the episode was still Kelli’s brief story about how she framed a potential friend who was dating one of her exes. “Renee is cool,” she calmly explains. Give me my Kelli-centered episode NOW, please.
  • Ahmal (Issa’s brother) is back! And they’re letting us know at the top he’s gay! The show has previously received criticism for letting his homosexuality mostly exist in subtext, so it seems like they’re trying to address that.
  • Lawrence is still around. I’m still not sure why I’m supposed to care about Lawrence, but neither situation involving him and Condola or Issa really interests me. Apologies to LawrenceHive. I know Condola is too good for him and I don’t even know her that well.
  • There’s no Daniel, but Molly does mention Nathan. He’s still friends with Andrew and Issa is not ready to see him.
  • I want that Waiting to Exhale t-shirt Issa is wearing in the first scene.
  • This season’s in-show show is Looking for LaToya and so far features Ray J as LaToya’s boyfriend and Terri Vaughn as the show’s host.
  • Welcome to season four! I’m glad Insecure is here to make our quarantines a little easier.

Ashley Ray-Harris is a stand-up comic and writer.

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