Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.

Molly and Issa face the future as Insecure wraps up an amazing fourth season

Jay Ellis (left), Issa Rae
Jay Ellis (left), Issa Rae
Photo: Merie W. Wallace (HBO)
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Last week, I said Insecure wasn’t a show known for raising the stakes. Over four seasons, the show has blurred the lines between comedy, drama and hangout sitcom. Molly, Issa and Lawrence have grown and changed, but they all still face some version of the insecurities they’ve always had. Last week, I said fans hung tight to theories like Condola’s pregnancy and Tiffany’s affair because they needed to believe the show could have more consequences where there actually were none. I, like a fool, did not believe Insecure would ever deliver on these fan theories, because why should they? The show was good at what it’s always done. With “Lowkey Lost,” Insecure shows viewers it’s good at something else.


This is by far Insecure’s best season and this finale is absolutely a treat to fans. “Lowkey Lost” provides nearly four seasons of plot momentum in one episode. After a season focused on the intimate details of Issa and Molly’s growth and friendship, it was inevitable that we’d see the duo face consequences for their decisions. They were both moving too quickly. Issa thought she had a future that wasn’t actually in her grasp. Molly didn’t realize her relationship was just another label she was clinging to until it was too late. Lawrence just...has awful luck I guess? Either way, a happy ending wasn’t in the cards for anyone. We all saw the doom coming, I just...I really didn’t think Insecure would have the courage to actually blow everything up like that.

Of course, Prentice Penny’s script could’ve had Molly and Andrew’s relationship explode over petty nonsense, per Molly’s past behavior. Similarly, Issa and Lawrence could’ve split up over Issa’s lingering uncertainty or an issue with his career. Instead, things are going perfectly for both Molly and Issa before they explode. The farmer’s market and work events are almost too perfect. So, in order to make the inevitable end possible, Penny gives Twitter everything they ever wanted: Tiffany is finally involved in some drama! Condola is pregnant! Kelli does things that matter to the plot! Penny’s script looks at seasons of viewer demands, promptly gives them to us and then puts the story right back where it always needed to be.

It would be frustrating if it didn’t absolutely work. Of course, I groaned when Issa found out Condola was pregnant, but if the season was going to end with Lawrence and Issa separated, why not go out in a blaze of glory? It doesn’t necessarily matter what keeps Lawrence and Issa apart, the point is that they’re not the people they once were. Condola’s pregnancy is forcing them to move on to the inevitable. If it hadn’t been Condola, it would’ve been the distance or something else. Issa doesn’t really want to leave Los Angeles, she’s just chasing an idea of happiness that Lawrence represents right now.

Insecure is asking viewers to move on too. That Prentice Penny chose to use the very fan theories that have dominated Twitter to force us to accept Issa and Lawrence’s new reality is brilliant storytelling. It’s also the perfect end to a season that gave Insecure more time and space to tell the story it wanted to tell. Even though Twitter fans called these possibilities out, they still didn’t feel like things Insecure would actually do. Penny’s script doesn’t just call our bluff, it makes sense of everything too.

With season four, Insecure has taken new risks. They’ve introduced us to more of Issa’s family. They let us see Molly in the relationship she’s always dreamed of having. With episodes like “Lowkey Thankful” and “Lowkey Happy,” they changed the very way the show could tell Issa, Molly and Lawrence’s story. So, it’s only fitting that such a daring season have such an audacious ending.


It also kind of makes sense that only something as heavy as Condola being pregnant would force Molly and Issa to reconcile. Molly’s break-up with Andrew wasn’t really shocking. Every irritation he brought up was something we’d already seen. He was also right, Molly doesn’t let anything go and Andrew isn’t about that grudge life. Molly has to accept that she and Andrew are on different pages in life and it has nothing to do with Issa or her career. Molly may not have been willing to do the work for Issa, but Andrew wasn’t willing to do the work for her. Still, if Issa had still been with Lawrence, she probably wouldn’t have welcomed Molly back so easily. After finding out about Condola, Issa probably only wanted to talk to Molly again.

I am sure many will be disappointed that Lawrence and Issa may not get their happy ending, but that’s the least interesting relationship story of the season. Insecure tore Molly and Issa’s friendship apart and managed to find stakes high enough to make sense of their reconciliation. Through all the relationship drama, pregnancies and Twitter fandoms, “Lowkey Lost” proves that black female friendship is still at the core of Insecure.


Episode Grade: A-
Season Grade: A-

Stray Observations

  • Right, Tiffany. I think the show could’ve done a better job dealing with her postpartum depression. It was mostly played as a blatant joke. It was hard to take the risk seriously since the last time we saw her, Derek felt okay leaving her at a block party drunk by herself. It’s the clumsiest part of the story, but Tiffany and Kelli always give Molly and Issa a reason to reconnect.
  • That being said, there was a moment when I thought maybe Tiffany was dead and I really didn’t care. She and Derek are simply tools here to force Molly and Issa to interact again. They serve no other purpose. Amanda Seales’ one scene didn’t sell the emotion of the moment either. Did she just need a staycation and a bath? Was it a full on mental breakdown? Did she cheat? It doesn’t really matter.
  • Ah, there’s the Old Andrew. I missed him. Go be free, Old Andrew.
  • Yvonne Orji, again, deserves a shout out for her work this season. Even though Molly got what she deserved, I felt her heartbreak. They did not make Molly easy to like this season, but Orji brought so much empathy to the role.
  • Nathan, you beautiful, perfect adult. He apologized. He communicates. He works in a very packed barbershop. Issa, you fool.
  • See, I knew Lawrence would mess things up somehow.
  • I love that Looking for LaToya’s only purpose was to be the catalyst for Molly and Andrew’s breakup. We don’t even know if they found her, but there’s a reunion episode?!
  • “Ossie Davis-ass nigga” - Kelli. Please, never change, Kelli.
  • The moment with the police felt like Insecure addressing the criticism that the show should be more political. Insecure shouldn’t have to tell political stories just because it’s a black show. The cop’s dismissal of the entire idea felt like a nod to that. Insecure just wants to be funny, just let Insecure be funny!
  • This really was the best season of the show yet, I think.
  • Guisados is really good.
  • That’s the end of the season! I’ve been reviewing Insecure since the pilot and it’s been interesting writing about it now that I actually live in Los Angeles. Plenty of people have written about Los Angeles as a character in the show, but I’m going to get a little personal and admit I got emotional when I saw my block in one of the shots. It’s been fun to grow with this show and I thank you all for reading along with me. I don’t even mind the accusations from LawrenceHive anymore.
  • Prentice Penny, if you’re reading this: You got me. Goddamn it, I did not think you’d really make Condola pregnant!

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