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Insecure’s Showrunner on the Season-Two Finale and the Funniest Joke That Got Cut From Due North

Prentice Penny.

Insecure’s second season ended with Issa moving out of her Inglewood apartment and into the apartment of her on-again, off-again hookup, Daniel. It was a jarring decision that came after the season’s most mature and meaningful moment: Standing in their old kitchen, Issa and Lawrence had one last conversation, finally making amends. “Just like in life: You take two steps forward, and then you make a decision that sometimes isn’t the smartest,” Insecure showrunner Prentice Penny told Vulture. “What’s interesting is we don’t necessarily know what her thought process is yet. That’s one of the things we may have more answers for in season three: Why she decided to [go to Daniel’s], what her viewpoint was going in.” Penny talked to Vulture about writing Issa and Lawrence’s finale conversation, jokes cut from the show-within-a-show Due North, and whether there’s something fishy going on between Issa’s friends Tiffany and Derek.

How did you decide on the structure of the finale?
We always try to find new ways to tell our stories. We liked the idea of playing with time. In episode four, “Hella LA,” everything took place in one day. As we talked about the finale, we kept coming back to all the stories we were trying to tell. It didn’t feel right tell all that in a super-linear way; something about that just didn’t work. Somebody pitched breaking it up in a Rashomon way, and doing it over a month. We asked HBO if we could get some more time — our episodes are around 28 minutes, and this would be closer to 40 or 45 — and they were super supportive. It happened very organically.

After their big fight in episode seven, Issa and Lawrence have a much calmer conversation in the finale, where they speak very honestly about their relationship. What was it like developing that scene in the writers room?
That was the conversation we knew people were wanting to hear and see them getting right. I think there’s this raw, this is it–ness. You know what it’s like when you talk to a stranger? Or you’re talking over the phone, or you’re chatting with someone on an airplane: You’re more willing to say anything because you don’t know them, or you don’t have to see them, or this is the only conversation you’ll have with them. It’s like, “I’m never going to see this person again so it kind of doesn’t matter.” I think that’s the conversation they’re having: There’s nothing more at stake, so you can be completely honest. That’s what we were trying to get at. There were these two characters who, from the series premiere two years ago, have not been completely honest with one another. Issa’s not honest about her feelings about Lawrence and where she is in her life, and Lawrence isn’t honest about his depression and where he is in his life. This conversation is happening two years too late, I think. Maybe if they’d said these things to one another early on, they’d be in a better place now. For us, it was like saying all these things these characters needed to say to one another for some time now, and just being honest to that.

Lawrence sends Issa a friend request toward the end of the episode. Do you see that as a peace offering or a final good-bye?
I view that as a peace offering, his way of asking, “Can we be friends?” Originally in that moment, Lawrence was going to move the couch into his apartment, and we still might do that at some point. The couch has a lot of symbolism on our show, so I’m not sure what we’re going to do with the couch. But I can probably guarantee that it will come back in some form in season three, because it’s a metaphor for a lot on the show.

In that moment, and I think smartly so, HBO said that there was never going to be a moment as impactful as [just after their conversation]. Watching it, you want to stay in Issa’s space. You’ve seen his side, and he’s thinking and feeling a lot. So instead we did the friend request. Is it a good-bye? I don’t think he planned that, but it was an, “Okay, I’ve closed that chapter, but I don’t have to block this woman out of my life as I did before.” So, actually, I think it’s an opening.

Do you think it’s possible for them to be friends?
I don’t know, we’ll have to check that out in season three, I guess!

The finale ends surprisingly, with Issa ending up at Daniel’s front door. What was your read on that scene?
We all have different opinions about it. One of Issa’s lines in episode seven, which I think is so true, is, “Why does our stuff always have to be messy?” There are people in your life, sometimes, where stuff is just messy. I think when you’re around Issa’s age, 29 coming up on 30, you’re trying to figure out, “Am I still this person I thought I was then, or do I need to start making more mature decisions to be somewhere different from where I am now?”

To me, Daniel represents the younger her. Sometimes it’s hard to end those things, to say, “I’m just not that person anymore.” I don’t think Issa’s there completely. The things she did with Lawrence, getting that closure, was very smart and very mature. It was good for her. But she also makes decisions that aren’t so great and aren’t thought out.

There’s another relationship I still have questions about: Tiffany and Derek. What’s going on in their marriage? Will we ever get to the bottom of what their deal is?
[Laughs.] Their marriage is great! What do you mean what’s going on in their marriage? They’ve got a baby on the way …

No, no, no! Out of the blue, Tiffany bailed on watching Due North with the girls, and in this season’s second episode she mentioned Derek was staying in a hotel for a little bit, and then Derek mentioned Tiffany had a work friend named Fred that he had to exchange words with …
Well, I think you gotta keep watching and something could come out, you know. [Laughs.] No! Now I don’t want to say anything, like this was never our intention! I’m seeing all these internet things saying, “Tiffany’s not carrying Derek’s baby! That’s that Fred guy’s baby!” It’s so funny. I kinda like seeing these Derek-Tiffany stans. We might lean into that more and keep people guessing about their marriage. [Laughs.]

The Fred joke that we had for Derek was an ad-lib we just did on the day. That wasn’t even in the script. They have married-couple problems! Sometimes you’ve gotta tell a dude, “Stop talking to my wife at her job!” Sometimes you stay at a hotel. For us, what’s so funny is that Tiffany claims she has this very bougie, perfect life, but there are these little cracks in her story sometimes, like, is it really that perfect? And if it’s not perfect, it sounds like there are some dark moments. And, you know, everybody knows that person who tries to act like their marriage is amazing all that time and it’s obviously not because no marriage is.

Speaking of feedback from fans online: Some fans have been disappointed with how Insecure doesn’t explicitly show the characters using condoms. Critics also said the conversation the girls had about blow jobs felt dated. Are you plugged into these conversations, or do you even listen to them?
In terms of it being dated, I don’t really know how to answer that. I mean, maybe? I don’t really know. Our show is mostly women and mostly black women, and most of them had a lot of opinions about the blow job stuff. The conversation in the room didn’t feel dated. When we were filming, it felt like a part of our show. It may not be on the same cusp as the Jared conversation, because that’s a much more progressive idea. But this conversation, to me, didn’t feel dated as we were having it in the room or when we were filming it. I don’t begrudge anyone for feeling that way.

On the condom front, I think our position has always been to assume that our characters are of a mature age and living in 2017 and assume that they’re mostly protecting themselves. We have 28 minutes to tell a story, and most of the time we’re cutting in right in the middle of them having sex. Very rarely — with some exceptions, I think, when Issa and Daniel had sex for the first time last season, or when Issa and Lawrence have sex this season — most times we’re hard-cutting into Tasha and Lawrence having sex or Dro and Molly having sex. We always try to place them in scenes when they’re in the bedroom, but we’re not a documentary, we’re not a PSA. But we’re trying to be responsible.

I get it: There’s not a lot of shows like ours, where you see black people and people of color having sex in a way that doesn’t feel melodramatic or Über-sexualized. But I also know that I’ve never seen this response to network shows. Why aren’t these people [asking the same questions of] Scandal or Empire or Ballers or Atlanta? Like, why isn’t the Rock wearing a condom? I didn’t quite understand the starting point. But with Black Twitter, you know, once something hits on Black Twitter, you’ve got to talk about it. I was getting responses saying that I don’t care about black people.

Oh my gosh.
I was just like, Wait, woah. This is going off to all kinds of topics that have nothing to do with what we’re talking about. Talking about safe sex is a worthy cause, and all shows should be talking about that. But our show is a comedy show that’s about this one character — we’re not always thinking about how to show the condom. Our thinking is, how do we get in or out of scenes faster, how can we save time or move the story along without a lot of steps. I think Issa’s response to the whole thing was great. We’ll always try to be responsible, but we’ll try to address it more next year, or make it more present in scenes.

How many Due North scenes did you end up filming?
I’ve lost track now. Originally there were going to be 12. There were going to be 12 scenes, and 12 little “next ons.” So you’d see a scene, and then there’d be a “next on.” HBO was like, you guys, this is not a real show, so we’re not going to take four days to film this show within a show. But they were supportive of the idea, so we did six or eight with the next ons. Pete Chatmon, who directed them, just embraced all of it. It was just the weirdest. I can’t believe we got Regina Hall and Scott Foley and Michael Jai White. They were amazing.

Did anything happen behind the scenes, or were any really good jokes cut?
Scott Foley had — it was just crazy. Once everybody started leaning into all of it. In that scene where Regina Hall is about to go down on Scott Foley and he’s standing over her, as she was unzipping his pants, he had one line that was like, “I need you to emancipate him!” All the crazy Civil War double entendres you can think of were in there. Michael Jai White had a line where he told Regina Hall that she let [Foley] “swing low on her sweet chariot,” but [White] had another one-liner, like, “you let him go below the Mason-Dixon.” It was just hilarious.

I’m obsessed with Molly’s therapist’s office. What can you tell me about that location?
It was great, I’m so glad you said that. The second we saw that location, [director] Melina [Matsoukas] messaged us and was like, “This is awesome.” We just all loved it. It was in the Palms area of L.A., not too far from Culver City. It was this little house, and the whole house was really cool. But that room was particularly dope. That’s what’s great about our show: We try to find different parts of L.A. that you just haven’t seen before. We didn’t want to have Molly doing it a normal therapist’s office. We liked the idea of her stepping into this world for the first time, and a home felt like a safer space.

This interview has been edited and condensed.

Insecure Showrunner on the Funniest Joke Cut From Due North