What's Really Going on With Issa and Molly's Friendship? 'Insecure' Showrunner Prentice Penny Explains

There comes a point and time in every friendship where something goes wrong, disagreements arise, tempers flare and besties fall out of sync. It happens—everyone isn't always going to get along all of the time.

But just like the trials that lovers endure and arguments among family members, the true testament of a friendship is how the people involved rise above the rocky moments. Can you find a way to apologize, hash it out and get back to the golden era of friendship you once knew?

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It's a notion that Insecure characters Issa (Issa Rae) and Molly (Yvonne Orji) will likely have to consider as the HBO series continues its fourth season.

Shady exchanges and explosive blowouts aren't foreign to the longtime friends. The women have dished back-handed comments to each other since the series debuted back in 2016, and every season they're in a fight over one thing or another, perhaps the worst—so far—being season 1's heated exchange at the We Got Y'all fundraiser, where Molly accused Issa of playing the victim and being unable to commit to a job or to her then-boyfriend, Lawrence (Jay Ellis). Meanwhile, Issa roasted Molly for lacking self-awareness and accountability. ("You're impossible to please!" Issa snaps in that exchange, to which Molly replies, "B***h you don't even deserve Lawrence!")

Season after season, though, the ladies always manage to talk it out and patch up their friendship. But this season feels different. For one thing, the whole season appears to be playing out as a flashback; one of the first things we see in the fourth season premiere is Issa on her couch at home along, talking on the phone to someone and saying she doesn't really keep up with Molly anymore. The rest of the season takes place before that moment, and shows us, over a period of months, how Issa and Molly got to that point.

First they have a little spat following Issa's block party mixer during the season premiere. Since then, it's been cheap shot after cheap shot, passive-aggressive comment after passive-aggressive comment. In the most recent episode, Issa bails on their annual Thanksgiving pie tradition—a sure-fire sign that their friendship is crumbling.

"There's a lesson to Issa and Molly's relationship," showrunner Prentice Penny told Newsweek of the apparent rift that's driving the friends apart.

"They know each other so well, and they've been around each other for so long," he said. "It's like when someone has all these memories and images of you from a long time ago and that impacts their reality. It's a history where they feel like they know everything about you, and they don't let you move on. They still hold you to things you did when you were younger as opposed to seeing where you are going."

Now in their 30s, both Issa and Molly are changing from the girls and young women they used to be, but neither has recognized the personal strides that the other is making to become a better adult. If they're not careful, their friendship might become nothing more than a memory.

Check out Newsweek's full interview with Prentice Penny below, and catch Insecure when it airs on Sundays at 10 p.m. on HBO.

'Insecure' Showrunner Explains What's Really Going On With Issa and Molly
(L-R) Issa Rae and Yvonne Orgji appear on "Insecure." Season 4 of the HBO series premiered on April 12, 2020. Merie W. Wallace/HBO

It's been almost two years since Insecure's season 3 finale aired. How was it getting back together with everyone for season 4?

It was great. We did [the first three seasons of] the show two years in a row, back to back to back, and obviously we were excited about that. But we realized that meant Issa [Rae, show creator] and I work on the show almost every month of the year. Even now, we're still finishing up and coloring and last-minute sound notes. So we don't really get as much time off of the show as a lot of other people get. It was starting to take—not necessarily a difficult toll, but a creative—toll on our lives.

We never want the show to feel stale or like we're repeating ourselves. And we also wanted to do other things creatively. I went on to direct my first film [Netflix's Uncorked]. Issa wanted to act in other movies. So we took a breather, and I think that really helped recharge all of our creativity because we came back to the show with much more excitement and ideas. We love working together and I think it made us appreciate the show even more.

It really does seem like Issa is maturing and trying to overcome her insecurities this season, but that seems to be creating a problem for Molly. Was this shift in their friendship something you guys always had in mind for the show?

It's something that we talked about. We're always trying to figure out—based on where the characters' been and what the characters' done—what they'd be doing now. What's the version of where they would be? So that's something we're always holding to. How would these characters be right now at this time in life? Are people in your life for a reason, a season or a lifetime? We try to kind of answer that this year in terms of our characters, with where they're headed in life. Is this somebody that I need to know in my 30s? Is this someone I need around for a reason? Or did I need to learn a lesson, and I don't need them anymore? That's something we always wanted to explore.

Are you rooting for those two to get past their issues?

I'm personally rooting for the show to always be honest. Whatever way that is, that's what I care about. I care about writing characters to be honest. I never really worry about having a happy ending—for me, that's never really the point. I want to watch the characters go on a truthful journey about themselves. The show's not going to go on forever. We're never going to get the answers to all of our questions. A happy ending for Issa or a happy ending for Molly—whatever the "happy ending" is—I think it will be truthful to Insecure. We're never going to do anything that people will be exactly, totally happy with when that time comes. We just have to be truthful and honest.

I love Jay Ellis but Lawrence literally burns me up. How are we still dealing with him and Issa and their mess after all this time?

What are they going through right now? [laughs]

It just seems like there's some bigger, underlining thing brewing with this whole Condola [who's played by Christina Elmore] situation. He keeps ending up in Issa's orbit after we already got our closure. Why is he like lingering?

One of the interesting aspects of our show is even though you guys haven't seen the show in a year and some change, in the world of the show overall, it's only been like a year. When the series started Issa was turning 29, and when Season 3 ended, she was turning 30. So even though audiences have been with these characters for a while, in our characters' world, it's been a year. In some ways, we have to be faithful to that and not act like it's been four years that [Issa and Lawrence] have been broken up, even though for the audience it's been that long.

That's one of the tough things that we have to be faithful and true to. They were together for five years—that's what Issa says in the [season 4] premiere. So if you were with someone for five years and you're broken up for a year, yeah, that person is just kind of weirdly still a part of your world. Lawrence is friends with Derek [Wade Allain-Marcus] and Issa's friends with Tiffany [Amanda Seals]. They're going to cross paths. That's just a thing that's going to happen.

These are the things that often frustrate people about TV, when it comes to behaviors we exhibit ourselves. We try to write to that. These characters aren't perfect. A lot of times people want characters to do things they wouldn't do themselves because we don't want to see ourselves—in some ways—in those positions. We're watching it and it's like, "Ugh, I would do the same thing. That makes me so mad." You're watching it in a much more honest way than when you watch your own life.

It's interesting because you and Issa have become so successful from the show, yet you're still dealing with characters who, unlike yourselves, are really struggling with adulthood.

Between all of our circumstances—Issa's friends and her relationships, my friends and relationships, all of our writers—there's plenty to pull from that inspires Issa and Molly's instances for sure.

How do you stay grounded after creating something that has had such an impact on pop culture?

Opportunities like this don't come every day, and we really are like a family. This journey we've been on is really like a special moment in time and you never know when moments like these are going to pop up again. So I know when it goes away, it goes away. When we started working on the show our goal—well for me, anyway—was to always make good work. And I only care at this point in my career to make good work.

I care about the ways I occupy that space—whether I'm writing it, editing it, whether I'm producing it, or just giving some notes—I just want to be attached and around people who are doing really good, cool, interesting and innovative things. That's been my focus. I just want to keep making good stuff, and I got plenty of family and friends that keep me way grounded.

How much longer do you want the show to go on for?

We haven't really talked about it. We know we don't ever want to overstay our welcome. Whenever we feel like we've told our story, we'll be over. But we don't have a number [of seasons] in mind.

This interview has been edited and condensed for the sake of clarity.

What's Really Going on With Issa and Molly's Friendship? 'Insecure' Showrunner Prentice Penny Explains | Culture