‘Insecure’ Showrunner Prentice Penny Explains What’s Next For Issa and Molly’s Relationship

Warning: Spoilers for HBO’s “Insecure” below.

The season finale of “Insecure” ran for the typical length of a half hour, but the episode was so filled with drama that it easily felt like 90 minutes. After beefing for most of the season, Issa (Issa Rae) and Molly (Yvonne Orji) were forced to come together to find their friend Tiffany (Amanda Seales), who has been struggling with postpartum depression. Andrew (Alexander Hodge) broke things off with Molly. Condola (Christina Elmore) told Lawrence (Jay Ellis) that she is pregnant with his child.

Fans are ready to see how Issa handles herself next season — is she ready to be a stepmom? Or will she pull Nathan (Kendrick Sampson) out of the friend zone? We talked with showrunner Prentice Penny about the climactic finale and what’s next in store for Issa, Molly and the crew. 

The season finale was the heaviest episode yet, so I want to talk about how we got here. What were you all thinking about in the writers’ room when making this episode come to life?

It sort of took various forms in various phases. The main thing we knew early on was that we wanted to get Issa and Molly to come back to the table. I mean that, almost literally. We wanted them to realize that these friendships and these relationships don’t grow on trees. They’re fragile. When you go through something in life, things kind of get put in perspective, of what’s really important, like the importance of communication and being open and seeing each other. 

So it just kind of took various forms, but we knew it was always about how do we get Issa and Molly to come back to the table without there being this sort of like heavy thing also, where they need to have a real “talky” reconciliation? Because there would be so much to talk about that we were just like, that doesn’t feel as interesting or dynamic. So we tried to use the Tiffany thing as a way to slowly bring them back to the table. 

Let’s about Tiffany and her storyline; she was dealing with postpartum depression for the entire season. Why was it important that fans saw her in this light? 

Postpartum depression is very, very common. I will say it was thought out from the beginning, before we wrote the season. One of the things that we did in Season 3 was we had Tiffany, who is this character who is married, was having a baby and also has made her life in some way feel like she needs to always seem perfect and seem like she doesn’t have any flaws … we wanted to examine what that looks like for a character who, if you remember in Season 3, the baby shower, she was built up on what it would be like to have a baby. We wanted to bring that crashing down.

We just wanted to make her really wrestle with connecting to her daughter and these issues because she thought in her mind it was going to be one way. And so we really wanted to play on this idea that nobody even asked her to be this way, but sometimes we put those things on ourselves. We can do things with Tiffany that we can’t really do with the other three women because she is married and she does have a baby. So that was always something, before we really got into the season in terms of specific stories, that was an area of her life that we want to talk about. 

How was working with Jay Ellis and Kerry Washington as directors this season? Can you talk about the importance of rotating directors throughout the season and what it adds to the show?

Yeah. I mean, they’re horrible. [Laughs.] I’m kidding. They’re great. We’ve always rotated directors. Every week, typically, there’s a different director. I think besides Melina [Matsoukas], myself and Kevin Bray, everybody’s done one. And we try to do that purposely to give more Black directors opportunities. Jay is somebody who knows the show, he’s been here since the beginning, watched a lot of directors. I was really excited about his episode because Jay and Yvonne are just really close friends in general, and it was also the episode he didn’t have to be in … he wasn’t in it really except for one scene. And so it just worked out nicely that it ended up being his episode. From an acting perspective, he was so amazing because he just knows how to talk to them. 

Kerry came and shadowed Season 2, during the finale. And she was just great. The actors just really responded to her and she just … is Kerry Washington. She brings great energy. She had smart shot selections to reveal things. And I had to direct behind her. So I was like, oh, I gotta really bring my game because Kerry is out here killing it. She’s amazing, smart, and pushed the actors in a way that I don’t think any other director we’ve had has really like pushed them because she’s such an amazing actress herself. She just knew how to talk to them in a way that was just very specific. 

The entire season focused on the strained relationship between Issa and Molly, but in the finale, it seemed like they were finally going to talk through their issues. What should fans expect for their relationship moving forward?

I think fans can expect them to have a more mature and humbled dynamic and respect for their friendship. I mean, Molly and Issa met in college. They met when they were 18. They’re in their 30s now. This is somebody you’ve been friends with for over a decade. And so, of course, you’re going to change. The whole season was about how certain relationships in life are either for a reason or a season, right. Or a lifetime. We wanted to say Molly’s [relationship is] a lifetime. 

But with that comes responsibility, with that comes humility, with that comes grace and understanding and growth. So I think you’ll see a lot of Molly and Issa 2.0, them being more adult friends than them just throwing daggers at each other, or just for fun. I think just them understanding like, oh, let me be careful about my words as opposed to just being cavalier with it.

After Lawrence revealed that Condola was pregnant with his child, Issa was pretty much stunned. Her whole idea of creating a nuclear family with Lawrence was blown up. It feels like the show is going in the direction of exploring deeper issues like complicated family dynamics.

I think it comes from this place, and I think we all have been there, like in your 20s, it becomes a time where you have to plan for your life. I have to be married by this time, I have to have this done by this time … And then you’re 30, you go like, does it have to look like that now? You just have more life experience; you have more real-world experience. And so what we are trying to do this year, I think is to say, OK, it may not look like this, but is that bad or good? It may look a different way. Am I settling or am I understanding that that’s how life is too? That it doesn’t have to look that way. Or am I saying, am I accepting that life isn’t so black and white and things are a little bit more gray, but what really makes me happy? You know what I mean? I think that’s the sort of thing you wrestle with as you go into your 30s. You realize things aren’t always so neat and clean and cut and dry in the way you might have idealized them to be.

With the coronavirus sweeping the nation, and the protests against police brutality springing up, people are turning to “Insecure” for a break from everything that’s happening in the world. How do you feel about the way fans have reacted to this season?

It’s a weird time. I think for a while, Issa and I were both feeling like the show, it felt like, who cares? Because there’s so many real world things that are going on and we felt super insignificant and understandably so. And not even from a nobody’s watching the show perspective, but just sort of like a real life one. Like there’s just bigger things: we’re not feeling super funny, we can’t physically be together right now, we can’t celebrate the show in the same way, but also just like, does the show matter right now? 

I think it was the episode of Issa and Lawrence, Episode 8, and that was obviously a really hectic weekend. And we just felt like, who cares? And so what was nice was people responding to seeing Black love and Black beauty on the screen that weekend. Even if it was just a half-hour break from the world, I was just really stunned at how many people still watched, specifically from that episode on. That episode airing that week to me was definitely God’s plan because it just was all about Black love, Black beauty, Black humanity in a week that did not feel that we were treated or seen as human beings. 

You put an end to the rumors about Tiffany’s baby. How closely are you all looking at the conversations on Twitter? 

Oh, we look at it, but it doesn’t shape our show. I look at it mostly for fun. Sometimes we’ll look at it, not from an “it shapes our stories” perspective, but sometimes we’ll think, oh, maybe we weren’t clear enough about this. Or maybe we missed something to explore but you can only do so much when your television show is 28, 29 minutes and we only do 10 episodes a season. I don’t think we ever want to write our show for social media. 

You all always tell your fans that they’re only going to get 30 minutes. 

Yeah! It’s so funny. I’m thankful that people want to see more of our show, but I’ve never, ever heard of a comedy usually being an hour. And I’ve never seen a comedy, all of a sudden, change its format in the middle of its run. So we’re always going to be a half-hour show, but I’m thankful people want more. 

People are already ready for “Insecure” season 5. How far along are you all in production, and what else can we expect from the next season?

Oh, we’re just in the writer’s room part. We’re just figuring it out. We’re not anywhere near close to production right now. We’re going to start production this year, but again, all of that is predicated on what’s happening in the world, especially being in California and our cases are spiking. I don’t know what’s happening. So I think all we can control right now is what we’re writing. So we’re like two episodes into writing Season 5. 

Have you all talked about how “Insecure” will end? 

Oh yeah. Issa and I, from the moment we signed onto the show, knew how long we wanted it to go, so we both know. We both know, we just aren’t telling anybody. [Laughs.]