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‘Insecure’ Boss on Season 2: Issa’s Single Life, Reuniting With Lawrence and Going ‘Smaller’

As the showrunner of “Insecure,” Prentice Penny spends a lot of time thinking about how to tell the stories of the young African-American woman at the center of the show — Issa Dee, played by Issa Rae — in a truthful, organic way. “Insecure” follows Issa as she tries to navigate relationships in her personal and professional life, from her best friend Molly (Yvonne Orji) to her now ex-boyfriend Lawrence (Jay Ellis) to co-workers like Frieda (Lisa Joyce). Though the show features a group of key characters, it is told from Issa’s point of view, often offering the audience a unique glimpse inside her mind during moments she would otherwise be alone.

“Issa’s our main character, and she’s our way into this world,” Penny tells Variety. “She’s single Issa now, and she hasn’t been that person before. It opens up a lot of new stories and new awkwardness and insecurity for season two.”

Ahead of “Insecure’s” second season premiere, Penny talks to Variety about Issa’s evolution, how critical acclaim of season one affected his writers room, and how something that started out a joke among his staff turned into a key plot point for the second season.

How does season two evolve Issa and her point of view as the center of this world, and how will we start to see other characters’ points of views come in as well?

Last year a lot of the show was more insular. So many things, with the exception of her work life, were incestuous, in a way — the Daniel of it, the Lawrence of it, the Molly of it. In some way, there were a lot of connected streams with everybody and the things happening in their lives. But this year, because of the break-up, we’re able to expand more into things that Issa’s feeling that she may not even share with Molly — and vice versa. We’re seeing the world branch out in those ways, but also we’re seeing Issa in unfamiliar territory — certainly where she hasn’t been in five years — and asking “Who am I? Am I the person who cheats?” but also “Who am I in my workplace?” Before she had a lot of complacency issues and was sort of aggressively passive at work, and this year we’re seeing her be more assertive and what happens when she course-corrects and goes too far. We’re able to see inside her world in a much different way because she’s in a much different place.

Would the show ever break format, even if just for one episode, to go inside the head of a character like Lawrence or Molly the way it does with Issa?

It’s so funny because we do have a link this year that is sort of [that], but I don’t think we’d ever go so far down the line that we’re completely out of the main perspective that is Issa’s because that’s our in to the show. While we certainly dive more into what other characters are feeling this year and what their story lines are that aren’t even necessarily connected to Issa, I don’t know if we’d ever deviate so far that you’re like “Oh, this is an ensemble piece now.” Issa is our main character.

So how do you strike the balance of which parts of her life to tap into, while still fleshing out everyone around her?

A lot of it is simply because the show is not episodic. We talk about themes and ideas that we want to explore before the season starts. We have that as a blueprint as much as someone does who says “I think I want to go to Italy!” You don’t necessarily know where you’re going to go or what restaurant you’re going to eat at or who you’re going to meet, but you’ve narrowed it down to Italy. So for us, it’s a similar thing where we know we want to take Issa on a discovery of discovery or forgiveness or redemption, and then we start to anchor where she’s at with her dating life and her work life — and also, too, what sort of things are we experiencing as people of color in these environments. Being a mostly African American writers room in Hollywood, we certainly understand what it’s like when there’s not that many of us. So it’s about taking all of that stuff [into the show] and looking at what would be interesting for Issa or other characters. First and foremost, this show is always through Issa, and then I would say secondarily, it’s Issa and Molly. Third, it’s Lawrence or the romance as something else that’s happening in her world. I don’t think we’d ever get work-heavy and focus too much on Issa’s job. But again, because we’re trying to tell this narrative about this character, it keeps you on [track]; we can’t go too far off into crazy stories.

How will Issa’s relationships evolve this season — not just with Lawrence but also with Molly?

We advance three months from where last season left off. It felt like the right amount of time where you’re not super pining after the person — or at least hopefully not — and your friends have heard you b—- and moan and cry for a long time. You have areas where you have to portray that you’re OK and you’re moving on, and the interesting thing is what if that happens but you’re still feeling things about that person [while] you know you need to move on. You’re sort of at that “What am I going to do now?” stage because you’re not in the fresh hurt stage, and you’re building new routines of being alone. So it’s about what you do when you’ve broken up with someone but you haven’t really talked about it with that person. There’s no closure because Lawrence and Issa got in a huge fight, and he was gone, and they haven’t had any interactions. But he has to get stuff out of the apartment, and for us what was interesting was the person who is doing something publicly to move on but privately it’s really just a façade. And with Molly  whenever there’s a real crisis in her life, Molly’s happy to be there. They’re there for each other in those moments. They’re on a journey of self-discovery together. So in my mind, at the end of the day, those are the moments that are so pivotal. Lawrence might come and go — as obviously he has — but the person who was with her at the end of the first season was Molly, and that’s who was there at the beginning [too].

Should the audience be rooting for Issa and Lawrence to get back together this season?

I think any time you have a romance in your show, you want your audience to care about the romance because if they don’t, then you have no horse in the race, and people don’t watch anything they don’t care about. But what we really try to do is just be honest about where the characters are and let that dictate the story — to be true to what that experience is like. And I think you’ll root for them as people because you genuinely see that Issa and Lawrence and Molly are good people. They make mistakes, but they actually care about each other. So you can actually care about them in a way that’s human and not just “Oh, they look hot together!” I think as long as the characters are showing that they care about each other, then [the audience] cares. And even if you’re not rooting for them to be together, you’re rooting for them to be at peace or get their lives together.

Were there any additional challenges to writing this season after the first season got so much attention from critics and on social media?

Issa and I had a conversation, and [since] everything that happened last year was so organic — we weren’t trying to do anything except tell human and fully fleshed out, nuanced stories — the question was “How are we going to do that again? Where is that going to come from?” A mistake would have been to try to recreate any of that, and so we decided early on to go smaller. You know, sometimes if you watch a remake of a movie, they’re recreating the original but not necessarily carving new, interesting ground. And so for us, yeah, we could have put together a beat that’s like “Broken P—-” but that’s not how “Broken P—-” happened. We found an interesting way to bring it back and be a theme. So, this year we focused on more of those smaller details of their lives and getting more nuanced. In doing that it helps you become more specific and makes your point of view stronger. Once we did that, we weren’t worried about comparing seasons.

Something that may seem small is the show-within-the-show that you introduce in season two. Issa is watching this drama that looks like it could potentially mirror the themes of her own life this season. How did that come about?

We have two writers in the room we always give a hard time — Ben Duggan and Dayna North — and one day they were eating lunch together in the quad under our office, and we started making jokes that they were a couple. She’s black, and he’s white, and his last name is Duggan and hers is North — like the North Star — so we started making jokes that they were having these clandestine meetings by the creek on a slave plantation. We drew a picture in the room of two hands in shackles breaking free — like when love wants to break free. And it was like we were watching this show in the room. We got Regina Hall and Scott Foley. It was just a bit that grew and grew and grew. It’s not [actually] a mirror to the theme, but what we like is that in the real world there are shows that people watch that’s in the zeitgeist where people are tweeting about what they’re watching, and we wanted to capture that. As opposed to real shows that you have to license, we just wanted to make our own thing. And what I like about it, the course of its season takes place over the course of our season, so its season finale wraps up in our season finale, and the people who are watching it at different points, their stories start to intersect. I like how we’re using it to integrate other people’s stories at various times.

Season two of “Insecure” premieres on HBO July 23 at 10:30pm.

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