Prentice Penny talks to EW about avoiding the 'too neat' ending
Credit: Justina Mintz/HBO; Inset: Randy Shropshire/Getty Images
Issa Rae - Insecure
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Well, that was hella entertaining.

On Sunday, Insecure wrapped its standout (and too short!) second season. After the first season of HBO’s “smart, nuanced” series followed the decaying status of Issa (star/writer/co-creator Issa Rae) and Lawrence’s (Jay Ellis) relationship, the long-time partners were separated and dealing with the fallout from Issa cheating with Daniel (Y’lan Noel). Initially appearing to be completely built around Rae, Insecure became a three-headed monster, allowing Ellis and Yvonne Orji to fully shine on their own.

This paved the way for the finale, which was split into separate sequences documenting one month in the life of each of the three main characters. It all culminated in the intimate and emotional reunion between Lawrence and Issa that ended with a heartbreaking montage of what the future could have held. But in the end, despite the mending of the relationship, the two went their separate ways, leading to the final shot of Issa going to crash on Daniel’s couch.

To get insight on the finale, EW chatted with showrunner Prentice Penny about Issa and Lawrence’s future, Due North a.k.a. TV’s best show-within-a-show, and the “surprising” controversy regarding the show’s practice of safe sex.

ENTERTAINMENT WEEKLY: What was behind the idea of the finale’s unique structure?
PRENTICE PENNY: We constantly like to play with the idea of how we use time in our episodes and finding new ways to tell our stories. We had started to play with time in episode four, where it was all taking place in one day. And we liked the idea of what else can we do with playing with time. When we started talking about the finale and where we were going in the end, we tried to tell some of these stories linearly and they just didn’t work. I’m not sure how it came up in the room, but the idea of doing three different stories and seeing how they would later lead together made sense. I hope next season we find more ways to play with the way we tell stories in every way: time, visually, anything interesting.

It worked great and built perfectly to the scene at the apartment between Lawrence and Issa, which could be seen either as closure or as the first step towards eventual reconciliation. How did you intend for it to play?
I never want to tell people how they should feel watching the show, but I think for us, it feels like they finally have closure on that chapter of their life. The whole series starts with Issa trying to change who she is and Lawrence is feeling depressed with where he is. She didn’t vocalize certain things in the first episode that she was feeling — and the same with him. And I think the scene in the apartment was them saying things that they had long been feeling. So it was really about this couple burying the hatchet and saying what they maybe wish they had said early on.

In the big picture, do you view them getting back together as inevitable or are you not yet sure what the future holds for them?
I don’t want to say completely… I definitely have thoughts [laughs]. But like in real life, once someone is in your life, they’re in your life until you decide to kick them out. I don’t know, I’m not actually sure what the future holds for Issa and Lawrence. I think that’s the fun thing about our show. What I liked about this year is obviously the first season you get to know these characters, Molly (Orji) and Lawrence, who are connected to Issa and they weren’t really in that many scenes without her. And what was nice about this season was following Lawrence in stories that didn’t really have anything to do with Issa. Some of it is tied to Issa, but a lot of it didn’t have to do with her, and it was cool that our show can work whether we have them together or not. But I think there will always be some sort of unsaid web that connects them. How we use that, I can’t really say at this point, but I think it’s nice that they’re starting a friendship now and I’m curious to see where we take that in season 3. Can they be friends?

Did you intend for viewers to even momentarily believe the proposal was real?
Yeah, our view point on it was if you believe it’s real, then you’re hurt and sad that it won’t be real or it isn’t real. And if you don’t believe it’s real, that’s okay too because you’re also touched now by the promise of things that will never happen. For us, it didn’t matter if you believed it or not, you’d still be impacted by Issa visualizing her future that will never happen. So we always thought that you’d emotionally connect to it on either side. Obviously, we wanted people to believe it was real for at least a moment. But there were people who believed it was real because playing with time in the episode allowed for it to be a possibility to some degree. Hopefully, people were touched by it either way.

Coming off this burying of the hatchet with Lawrence, Issa makes the surprising decision to move in with Daniel, the person she cheated with, not to mention the unpleasant interaction they shared more recently. So why have her move in with him?
What’s so interesting is looking at Twitter on Sunday, people were like, “Oh my god, that’s such a bad choice.” When you’re 29 or 30, you take two steps forward, one step back. Nothing is like, “I have this moment of epiphany with Lawrence and now every decision I make for the rest of my life is going to be sound.” You still do things that are perplexing or confusing. What’s going to be nice in season 3 is you don’t really know what Issa’s mindset is when she moves in with Daniel. Their relationship was always kind of messy in a weird way, which she even says in episode seven. Issa and I have things we want to do with Daniel arc-wise in the series and we’re trying to implement some of that. And the same with Molly. Her answering the door with Dro (Sarunas J. Jackson) is also where she took a few steps forward. She tried with Quentin (Lil Rel Howery) and who knows how it’s going to play out or if she’s also going to continue seeing him or what her mindset is now with Dro. She definitely thought she could handle it, but her answering the door that way doesn’t necessarily tell me she’s still a sucker. She might be trying to put Dro in his place. What’s going to be fun is to leave people in the spaces of “Where is this going” or “Why is this character making this choice?” To me, it would almost be too neat for our show if you had this beautiful moment between Lawrence and Issa and this really beautiful moment with Issa and Molly, and the end of the show is everyone being great [laughs]. That’s not always real life.

Do you ever just want to give Issa a win? In this episode, she loses her apartment, her title at work, and maybe Lawrence for good. How do you balance the positive and negative in her life?
The first season of the show, Lawrence was horrible to a degree and everyone loved Issa. By the end of the season, the Lawrence Hive kicked in. One of the things we tried to do this year was debunk that Issa is perfect. Obviously, Issa Rae the person is charming, intelligent, beautiful, and smart. But, Issa Dee, the character, is a different person. That character sometimes makes bad choices and sometimes makes good choices. This is a character who started the season with such a horrible thing that happened with her relationship and is hurting while she tries to pick up the pieces. She doesn’t have closure with Lawrence and instead of dealing with the real emotions, she tries to be out there, but that’s not really in her nature or Lawrence’s nature. He has a lot of L’s too this year. It’s about, where do the wins happen? Issa does have a win in getting closure with Lawrence. Issa does have a win by deciding to stand up to the vice principal and realizing what is right. When Issa started to think she could be with another man, that was a win for her. The wins come, but sometimes they’re just moral wins or “I’m taking a step.” Often in life, the wins are small.

Playing a big role in the finale is Due North, which might be one of my favorite shows on TV. What was the genesis for that idea?
We have two writers on our staff: Ben Duggan, who is white, and Dayna Lynne North, who is African-American, and they just have a fun contentious relationship in the room. They love each other, but always give each other a hard time. They were having lunch together one day and we all started making these jokes that this was a secret slave romance lunch. And they started making voices of what they would sound like if they were having this master and slave romance. We thought it would be a funny television show; not for our show, just in general. We would reenact scenes in the writer’s room for kicks and we decided to call it Due North because of their last names being Duggan and North. We kept doing jokes and eventually said that’s the show everybody should be watching. Underground, Scandal, and Empire are on at the time, so it was like an amalgamation of all those shows. It was really super organic.

How did you go about landing Regina Hall and Scott Foley for the roles of Ninny and the master?
When Regina Hall first got the call, she thought she was going to be on Insecure the show. She was like, “Yeah, yeah, I want to be on Insecure! Wait, Due North, what is this?” And so, she read it and thought it was super funny. We also wanted Scott Foley, and they’re at the same agency and know each other and both just agreed to do it. They were both just amazing sports. I can’t believe that they did it, but they sell it. They’re the reason why I think it’s so great.

What did you think of this “lack of condoms controversy” that seemed to come out of nowhere to become a weird internet thing? What was your initial reaction to hearing about it?
At first, I was really shocked because there’s really not that much sex on our show. I think it was episode 3 and we had done three sex scenes, so it averages out to one per episode. In my mind, I was like, in the writer’s room, we always talk about our characters having safe sex, and obviously, there’s times where you don’t and that’s reflected in our show, too. But we’re certainly not promoting or advocating it and we always try to have condoms in the background. We’re not a documentary or a PSA. We’re not always going through the actual steps, and sometimes, we’re jumping into the middle of it. Rarely do we see it play out in actual real time. We also assume that people in 2017 are having safe sex or don’t need a television show to tell them that. I have never heard this about Atlanta, Scandal, Empire, or any other cable show. I think it does show how much people care about our show. Also, the sex on our show feels very real and you don’t often see people of color having sex that way like some of our white-counterpart shows have all the time. There’s a visceral reaction when you see it that feels very real. I love that people care about those issues and hope that people are practicing safe sex, but it definitely caught me off guard. Twitter is like that — the good and the bad. It’s a brush fire. I couldn’t tell if this was a thing that’s just happening on Twitter or a thing that millions of people who watch our show feel and think. You have to be careful, because if you try to go up against Twitter, especially black Twitter, you lose out the gate. It’s too big of a force. So you just try to do what you can and I think Issa’s response was great, which was, “We aren’t promoting that and we’ll try to be more aware of those things next season.”

Insecure has beenrenewed for a third season on HBO.

Issa Rae - Insecure
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