Insecure Showrunner Prentice Penny on That Explosive Issa-Lawrence Fight, Making Audiences Uncomfortable, and Why the Show Is Scaring Men

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Spoilers for the latest episode of Insecure ahead.

When Prentice Penny first signed on as showrunner for Issa Rae's HBO show Insecure, he was shocked to learn from bouncing story ideas off his majority-female writers room how petty women can often get with each other in times of conflict. He'd previously written for Girlfriends, but the politics of female friendship have regressed quite a bit since then thanks to social media. And when the gloves are off, the blows aim low. That disregard for a filter or emotional empathy was played to dramatic effect on Sunday's excruciating penultimate episode, which saw the show's core relationships implode in what feels like slow motion. Insecure's foundational sisterhood between Issa and Molly cracked in half when the two finally decided to drop decorum — prompted by Issa's suggestion that Molly try therapy — and give a harsh read on each other's mistakes that they've been holding back all season.

But it's the already-strained relationship between Issa and Lawrence that took the ugliest turn, when, by chance at Issa's work fundraiser, Lawrence suspects she's been unfaithful. It results in a turbulent confrontation from which it seems unlikely they'll ever recover. Vulture spoke with Penny, who wrote the episode, about dissolving the show's central relationships, making viewers feel uncomfortable, the changing L.A. landscape, and why Issa's actions on the show are making men scared.  

Walk me through the process of writing Lawrence and Issa's explosive fight.
We knew this would be a big moment. Lawrence starts off pretty unfavorable — he doesn’t do anything for Issa’s birthday and she’s about to break up with him. Going deeper in the series, we had to dig him out of this hole because we wanted you to be invested in how that relationship turned out. You can’t be invested if it seems all one-sided and you never understand Lawrence’s perspective. From his perception as a guy, as we approached this episode, Lawrence thought he and Issa were good weeks or months ago. But Issa slept with Daniel. Now it’s such a feeling of betrayal. When we were writing that scene, we had to be honest to their history and be honest to a guy who hasn’t yet pieced it all together and is figuring it out in the moment that his girlfriend cheated on him. We wanted to create a feeling of drama without it feeling overdramatic. I really wanted to portray this idea of how, in arguments like that, nothing is really logical. Fights heat up, they calm back down again, they go sideways. So you do things that are out of character because you’re feeling out of character.

I myself have been in a relationship in college where I got cheated on and I kicked over a table. That was real. And it’s also scary, which is another thing we talked about in the writers room. We didn’t want Lawrence to look like he was going to hit Issa, especially not after the fake fantasy she had in episode six. We’ve always seen this sort of safe Lawrence, and it was important that we see a side to him that we haven’t seen. He’s upset, he’s angry, he doesn’t know what to do with his emotions, but obviously he isn’t going to hit her. We wanted a feeling of unpredictability in this moment. What is he gonna do? We just don’t know. Those breakups are ugly. We’ve all blocked a door or thrown something. It just feels … crazy.

When Kevin [Bray] directed it, he got Issa and Lawrence in a great space. Also they’d been acting together for several weeks at this point, so they were close just as actors on a set. So to have this fight — and it was actually one of the last scenes we shot in that episode — it was feeling like a real betrayal and breakup. I think they did that scene ten or 12 times, and by take seven it was just like, “How are you guys still doing this?” I was continuously blown away by how amazing they were. But it was hard to watch. It was a very quiet day on set.

Did you intend for these fight scenes to be as uncomfortable for the viewer as they are for the characters involved?
This was initially going to be the finale, but HBO likes to have penultimate episodes be the big one, which was interesting because that means we’ll be dealing with the fallout from these fights in our finale. So for us, it was a matter of how do we ratchet up tension for the aftermath? Things are going great for Issa at her fundraiser literally up until the moment Daniel walks in. And that’s almost halfway through the episode, so once he shows up, it’s like, okay, now we can start turning the screws. How do we make it as uncomfortable as possible at every single turn? How does she keep him from Lawrence? And what’s Molly thinking? 'Cause she’s also not in the greatest head space. Plus Issa’s at her job, so she knows right away this is bad. But we knew we had to keep turning it up with Molly and then with Lawrence and Daniel. Originally, that scene between Lawrence and Daniel was going to happen in a bathroom because we liked the idea of two guys being at a urinal — it’s already uncomfortable. You’re the only two people, it’s very tight quarters, and you don’t know if Lawrence is going to kick this guy’s ass or what. But even after we changed the location, we still wanted to keep that tension going in every single scene.

Was there anything said in either of the big fights that Issa or someone in the writers room objected to?
Originally, the Molly-Issa fight ended with Molly saying, “You don’t even fucking deserve Lawrence.” And then Issa going “fuck you.” But it felt like because Issa’s the one who’s constantly the reason for her own demise — she makes bad decisions about her life to the point where even being passive is a bad life decision — me and writer Ben Corey Jones came up with Issa saying, “Are you just jealous that I can actually keep a nigga?” We had it typed up on the screen and I remember another female writer literally jumped up and was like, “No, no that is bullshit! She can’t say that, that is friendship ending. If my friend said that to me, that would be the fucking end of it!” We debated it among the four of us and it became this huge thing. We took it in the other writers room to Issa and another writer and we even debated it in there. We sort of had this monster in the room and I said, “Look, if it makes us uncomfortable and we’re clearly all disagreeing, that’s interesting. That’s what people will watch it and do.” We settled on that idea because we’d already debated for an earlier episode about whether, with Jered, if him getting a blow job makes him gay. We decided that we have to do things that are making the room uncomfortable.

At the table read, it was like, oooohhhh. Cause even Molly’s line — “You don’t deserve Lawrence” — is pretty aggressive, but Issa hits Molly in a place that’s kind of unfair. What Molly said may be true, Issa did cheat on him, but Issa’s insult is pointed at Molly’s character. There’s something flawed in you that you can’t actually keep a man. It was like Molly brought a knife to a gunfight.

Men seem to be reacting strongly to seeing a woman be the cheater rather than the victim. Was that a controversial story line to pursue?
That’s exactly what we wanted to show. It’s true that it happens, we just don’t see it. I think women are smarter about their affairs. Guys are stupid when we cheat. What I’ve been fascinated with is the response on Twitter to what Issa did. I think typically you associate a woman who cheats with someone who’s either super-vampy, some made-up doll, or like a Love & Hip Hop person with Gucci purses. What’s been difficult for men is that Issa looks like their girlfriend. Issa’s a regular chick who’s like, “Yeah, I have sexual needs and fantasies about another guy.” She looks regular and that’s the point: Issa could be
my girl. Men are like, “Oh shit, is there a Daniel in my girl’s life?” A lot of guys are putting themselves in Lawrence’s shoes because here’s a guy who turned down Tasha when she was making her advances. And that’s the thing: Guys always get shit cause they’re out there cheating, but here’s a guy who’s doing the right thing, and even he still gets cheated on. They don’t expect this from someone like Issa, but she’s just a person. Anybody can do this. It’s probably hitting a little too close to home for guys.

Without giving too much away, I think men will applaud the outcome of the finale. Have you ever felt pressure to attract a male audience via what happens to Lawrence?
Before the season even aired, we went to places and guys would be like, “Oh, this is gonna be male-bashing.” 'Cause then you see the pilot and there’s a guy on the couch not working. But actually, no! In this show, the girl’s doing the dirt. We had to let guys discover that. But I don’t think we’ve sat there and been like, “We need to make ‘him’ feel good.” It’s always been about what’s the interesting, honest choice. Our thing was always to let Lawrence feel the most real, not so much the need to redeem him or give him a victory.

This episode is set in Baldwin Hills, an affluent black neighborhood in L.A. Issa Rae previously told Vulture how hard it’s been scouting locations for Insecure because the areas are changing so rapidly. You’re also an L.A. native. Have you found that the city is changing faster than the show can keep up with?
We’ve always wanted to show the city’s beauty and its flaws. Typically when you see these places in a movie — Inglewood, Baldwin Hills — it’s not as beautiful. Your mind goes to
Entourage and Beverly Hills, as if that’s the only L.A. that’s beautiful. But there’s beauty south of the 10. It was very important for us to reflect that. But that neighborhood is constantly changing. Issa and I live in Inglewood and my house, literally if I jump over the retaining wall, I’m standing in the parking lot of the new football stadium. That’s how close I’ve watched this change happen on a constant and daily basis. That’s why we integrated the idea of gentrification and had Molly say, “I just saw white people up in Baldwin Hills.” That’s really happening. When I was growing up, you could go to a Krispy Kreme that’s by the Baldwin Hills Crenshaw Mall, and a couple of days ago, I just saw a white family walking their dog in that Krispy Kreme. You would have never seen that! This is Crenshaw. Right across the way is a weave store! This is just not what Crenshaw is supposed to look like, but it is. It was fun for us to incorporate that reality into the show. HBO encourages that.

This interview has been edited and condensed.