Insecure boss on season 4 finale, Issa and Molly's friendship

Warning: This article contains spoilers from the season 4 finale of Insecure.

There was nothing low key about Insecure's season 4 finale.

In Sunday night's "Lowkey Lost," Issa (Issa Rae), Molly (Yvonne Orji), and the gang frantically scoured the city for Tiffany (Amanda Seales), who disappeared while suffering from postpartum depression. On top of that, Molly and Andrew (Alexander Hodge) broke up, and Condola (Christina Elmore) threw a wrench in Issa and Lawrence's (Jay Ellis) rekindled romance. Thankfully, though, in the wake of all that drama, Issa and Molly, who have been on the outs for most of the season, finally sat down to talk out their issues at their favorite Ethiopian restaurant as the episode faded to black. So all's well that ends well right?

On Monday, EW hopped on the phone with Insecure showrunner Prentice Penny, who wrote and directed "Lowkey Lost" to discuss what's ahead for the reunited friends in season 5 and more.

ENTERTAINMENT WEEKLY: Issa and Molly’s relationship is at the core of the show. Were you worried that testing their relationship would shake the show's foundation too much?

PRENTICE PENNY: We actually leaned into that because we’ve always tried to make sure each season feels like it has its own energy and vibe. For us, I don’t think we think about it too much. I don’t know if that’s good or bad. We just think about things that interest us, and if we find it interesting maybe the audience will. But we never thought too far past, “This was interesting to explore.” Sometimes shaking the foundation is great. You want to see if that foundation can stand.

The finale ends with them finally coming together to have a conversation that's long overdue. Is there hope that they can get back to where they were, or has this experience changed that relationship a lot going forward?

We’re talking about that a lot in the writers' room now. The thing I think we sort of gravitate to is this idea of we don’t want them to go back to where they were. They’re going to be forever changed by this, forever humbled by this, and hopefully, forever close by this. I don’t think it’s about getting them back to where they were. I think we’re always going to have a version of them having fun together because they’re friends, but I think we want to explore what is that road back like and how is that road different. That’s the biggest thing, and it’s actually the most fun thing we’re talking about in the room right now – How do they have fun now, and not in a way that’s not them? Inevitably at the end of the day, you can have a fight with your mom or your friend or your spouse, but you’re still you. We’re not changing the foundations of who they are as people. We just want to be honest and true to how they would interact with each other now and maybe instead of less shade jokes to each other, maybe it’s a different shade of comedy or a different tone that they’re speaking to each other now. That feels fun because it’s a new discovery for them, too, as it will be for the audience. But I don’t think it’s about letting them be where they were. I think we’re trying to let them be like a 2.0 version of themselves.

A lot of fans started guessing Condola was pregnant a couple episodes ago. Were you surprised that they picked up on that before this episode, or did you hope that would happen?

No, I was pretty surprised people picked up on it because it wasn’t like anything we were leading to. It’s funny because when we write the episodes, we’re just thinking about what logically makes sense or what’s an interesting thing. When we were writing it, we didn’t realize [fans would guess it] until after we’d written the scripts because when Condola’s calling Lawrence in [episode] 8, she wasn’t calling to say she was pregnant. She didn’t know she was pregnant then. She was actually calling to get back together. In our world, she found out in between episodes 9 and 10. So [episode 8] wasn’t the moment she knew. But then when we were writing it and filming it, we were like, "People are going to assume this is what they’re calling about...Well, there’s nothing we can do about it now because that’s the way the script is written."

When I watched the finale, I assumed Issa and Lawrence broke up, but my coworker didn’t interpret it that way. How should we interpret that final moment for them? Is this the end of Issa and Lawrence?

I mean, you have to wait until season 5. Where’s the fun in that?

So it’s purposefully ambiguous?

Yes, it’s purposefully ambiguous, that that’s the moment we leave the scene. You don’t know what was said because we don’t really go into the next day. Really, Molly calls her the same day and they get together that night. We never saw them say, “This is it.” We just go out on that moment. The stuff we want to explore in season 5 is, what happens now?

I assumed they broke up, too, because during the Wine Down, Issa said this taints Lawrence in the character Issa’s eyes because this is a milestone they won’t have together.

We talked about that in the room a lot. If you remember the season 2 finale, she imagines this whole life with him, which is like getting married, having their first kid together. Now that fantasy she had in her mind will never be true because now he’s going to have a baby, or at least is pregnant with somebody else’s baby. Now [she’s thinking], can I still have what I want even though it may not look like how I want?

Was the intercutting between Lawrence’s conversation with Condola and his conversation with Issa scripted?

That scene actually took a little bit of an evolution. When we originally broke it, we broke it as two different scenes. You would see Condola and then him coming to tell Issa, but somehow it felt flat hearing it twice. From a visual standpoint, I just pitched, “What if each scene is answering the question of the next scene or giving you more information?” That felt more dynamic. Visually, I was trying to shoot that scene so if the question was asked, each corresponding shot that took you into the next scene would match the frame. So if you were in an over in this, you’d answer in an over of that; if you were in a profile or whatever the shot was, I just wanted you to always think they were all talking to each other collectively. One of my inspirations for that was in Spike Lee’s Mo Better Blues, there’s a great scene where Denzel [Washington] is kind of in this triangle between the two women he’s dating in that movie. He’s having sex with both them and he’s kind of forgetting his answers with one. I always loved that sequence and so I was like, “What if we tried something like that?”

During the search for Tiffany, the gang has this brief encounter with the cops, which made me hold my breath. How did it feel to watch that scene back last night amid all of the protests in the wake of George Floyd’s death, especially because the scene takes a comedic turn?

We filmed that scene in December and it was so funny. “Not me, not today," that line last night when I watched it, I was just like, “God, we wrote this police officer so much more aware than most police officers right now.” Because you’d think in today’s climate, especially with what just happened in Atlanta again, you’d just go [as a police officer], “Yeah, not me, not today. I’m not gonna end up on the news. Like, let me just handle this a different way. Let’s not make this be a thing that doesn’t have to be thing.” You just go, “Man, I wish so many other things right now [and that] police just handled it like people are human beings.” But yeah, it was very surreal watching it a little bit in the climate that we’re in.

The search for Tiffany made this episode feel a bit more fast-paced and unlike any other finale you guys have done before.

It’s funny, that was actually the intention. Originally, this episode was supposed to lean more into the Looking for Latoya [style]. The whole Looking for Latoya [story around Tiffany], we shot very docu-series style. There’s much more whip-pans and not really cutting a lot, you really rack focusing a lot. I really wanted to shoot it like a docu-series, and it doesn’t really have a lot of the Insecure framing. It’s much more handheld, whereas the book-endy parts before they find her and after they find her are all shot back in our standard way. We really wanted to create that feel. When Derek is telling the girls what happened, we actually shot reenactments. We shot the reenactments to look like Looking for Latoya, but it was with Tiffany. Those got cut for time and some other reasons, but we were really leaning into the docu-series of wanting to keep the pace very quick.

Going into season 5, you have a lot of history to draw on for story. What else can we expect from the next season?

I think we’re trying one of the questions that’s still sort of hanging from this: The Issa-Lawrence Issa-Nathan [relationships]. And can [Molly and Issa’s] friendship be better and what does that look like? Can Molly find love in a way that she doesn’t have to ruin it for herself and can she start to address the issues she really needs to address? Can Issa have success professionally? Really, the thing we’re playing with is, again: If life doesn’t look like how you imagined it, does that mean it’s a success or a failure?

Has the internet reaction shaped some of those discussions? Like there are people who love Nathan.

We always talk about what we thought would be a hit and what we didn’t really think about, and how those things play out. One of the things we’re still baffled about is people really thinking that’s not Derek’s baby. We don’t understand why people think that. We think people want more soapy drama, but we’re like, “We’re not that show.” We made an off-handed joke about some guy at Tiffany’s office that liked her and that was it. But now it’s become like, “That’s not Derek’s baby!” and we’re just like, Jesus, that was a joke in episode 2! In no world did we think when we wrote that joke that was going to mean that’s not Derek’s baby.

Insecure was renewed for a fifth season on HBO.

Related content:

Insecure boss says Issa and Molly can never 'go back to the way things were'

Related Articles