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Prentice Penny Says There's No Version of Insecure Where Issa and Molly Don't Love Each Other

The Insecure showrunner breaks down that bombshell Season 4 finale and gives us a glimpse at Season 5

Krutika Mallikarjuna

The fourth season of Insecure shook fans to their core. Despite the fact that viewers are used to taking sides over the men in Issa's (Issa Rae) life -- Lawrence (Jay Ellis) vs. whoever the fine ass flavor of the month is -- Season 4 delved into a breakup significantly more earth shattering than a romantic one. As Issa and Molly (Yvonne Orji) were finally reaping the professional and personal benefits of their hard work, they found they had grown so much that they didn't quite fit together anymore. 

"All the relationships in the show, are they for a reason, a season, or a lifetime?," said Prentice Penny, showrunner of Insecure, in a phone call with TV Guide. Until Season 4, viewers assumed Molly and Issa were ride or die, until the foundational cracks in their friendship surfaced and we realized that all those small grievances now meant the best friends would spend most of the season apart. The finale, which aired June 14, was the most brutal attack in a series of paper cuts; Molly went so far as to tell Issa that if their friendship is taking this much work, then maybe it would just be easier to walk their own paths. 

In the finale, the pair are brought back together suddenly when all of their friends gather to search for Tiffany (Amanda Seales) after she disappears, leaving her husband alone with their new baby for an entire night. Seeing how fragile even the most committed relationships can be -- especially after Lawrence tells Issa that Condola (Christina Elmore) is pregnant, and Andrew (Alexander Hodge) tells Molly he wants to break up -- forces the friends to realize that whatever they have, no matter how damaged, isn't worth throwing away entirely. The finale ends with Molly and Issa meeting for Ethiopian food, ready to talk without the fake camaraderie they've been throwing up in defense. 

From postpartum depression to unplanned pregnancy to shattering egos, the Season 4 finale was full of bombshells. Penny caught up with TV Guide to dish on all of them and give us the lowdown on where these complicated relationships -- especially Issa and Molly -- could go in Season 5. 

Yvonne Orji and Issa Rae, Insecure

Yvonne Orji and Issa Rae, Insecure

Merie W. Wallace/HBO

Tiffany's postpartum depression storyline this season was so subtle --  even in the finale, at the end of that frantic search, nobody's named the change we've been seeing in her in Season 4. Why did you decide to approach it that way?
Prentice Penny:
In Season 3, Tiffany had these amazing plans of what motherhood was going to be like and she had this over-the-top baby shower. She'd had this amazing view of what being a mother is going to be, but we really liked the idea of, well, what if we shattered that? Shattered [that picture of motherhood] for her, like it is for a lot of people? Whether it's marriage or having a child, everything has to be so perfect for Tiffany, so we wanted to show that everything is not perfect for her. Tiffany's a character who hides how she's really feeling, and so we had kind of been seeding that the whole season.

We also didn't want the episode to feel like we had an answer for it. Originally we had a scene where Tiffany, when they found her, she was saying a lot of these things she was feeling. But then somehow the scene just felt false, it felt like nobody does this in real life. It's not that simple to just solve postpartum depression. And so one of the things that we did was, we actually gave a lot of those lines to Derek. The lines that Derek is saying on the bus was originally Tiffany. What he's saying -- I didn't really pay attention, I didn't see the signs, I kind of wanted to ignore it -- and you could easily see Tiffany saying similar sentiments. We just wanted to move forward a step, which is finding her. A step is just her acknowledging she's hurting or this is really hard for her and she's sorry. And I thought Amanda Seales just delivered so well. The performance is great. 

We don't pretend to have the answers on our show, we're just saying these things are issues. Hopefully they promote conversation. The point was to always kind of play it much more understated rather than, here's the solution. And we tried to take a similar approach to Nathan and his mental health. We really want to normalize these things and not make them feel like they're sensational plot points. You know, that they're just, hey, these are things that human beings deal with. We want them to be things that people can have conversations about.

Will we see Tiffany in therapy next season dealing with postpartum depression directly?
We're talking about it now. We're in the middle of just breaking out Season 5. We're just now arguing out that stuff, but we're definitely not going to dismiss it. I don't want to ruin anything, but we're taking a very different approach to Tiffany next season, and how she is post postpartum.


Amanda Seales and Wade Allain-Marcus, Insecure


Season 4 brought Issa and Lawrence back together so beautifully. It seemed like Season 5 was going to be about setting up long-distance relationship problems and testing their new commitment. But you guys went in a totally different direction by threatening their stability with Condola's pregnancy. What made you switch gears to an unplanned pregnancy? How did you break that in the room?
If you remember in the Season 2 finale, Issa still sort of has this fantasy of what it's going to be like to be with Lawrence. There's a montage imagining their life together. They're going to have a baby and get married and all these things. So in Season 4 we wanted to explore this idea of: It looks like Issa's [romantic] life it's going in the right direction, but sometimes life has a tendency to be like, yeah, nah, we not doing that. Sometimes you have plans, and life goes, f--- your plans. And we wanted to ask, well, what does it look like if Issa's fantasy gets tested? What does that look like in Season 5? What does that do to Lawrence? You know, Lawrence is the character that usually likes comfort and is kind of a creature of habit. What does that do to his world?  

We just felt like their road back together was a little too clean and we wanted to see, well, what does it look like if the fantasy doesn't match what Issa and Lawrence imagined. Can you still love it? Can you still find the beauty in it? 

The episode ends on a really sad note for them when Issa says the pregnancy is too much -- but they're not really done for good right? 
Penny: We didn't want to answer it in the finale because with all that history, it doesn't happen that way. You have this moment and you cry, but we don't know what Issa and him said before he left, you know what I mean? I just think like life is not that clean. The truth is that that's a painful moment between them and they don't necessarily know what they want to say in that moment. A lot of times in that kind of situation you're just like, I just need to be alone right now. That's how I think that moment actually ended in real life. Clear their heads rather than trying to say, "We're going to be together or not be together." That's just too soon. Issa is just now learning about the pregnancy. We answered some things and we set up some other things that we want to explore next season.

The scene where Lawrence learns about the pregnancy from Condola is really compelling for similar reasons. He doesn't have the perfect response. He never says, "I'll be there for you no matter what you decide."
That scene was so much fun to shoot because we just kept saying, "What if we tried it this way?" I remember on the Lawrence and Condola scene, we rehearsed for like an hour, just trying the scene in different ways. We spent the first half hour just talking about the scene, the moment, where they have been, and what they might be feeling before we even rehearsed anything. And then we spend another half hour figuring out the rehearsal part and like trying things like, what if Lawrence is basically trying to force Condola to have the abortion? What is it like if Lawrence is really trying to be very logical and then when she's not being logical, he blows up? And then in the Issa and Lawrence scene -- Issa, what does the scene look like if you can't even look at him? What is it like if all Issa does is stare at him and read his face? 

All those little nuances just brought something different to every take, it was always about just trying to find what's the most interesting part of whatever version. The finale is mostly mismatched versions of trying those intense scenes in different ways. On the day I remember you could hear a pin drop when we were filming both of those scenes. Every version was like, Jesus, this is... I remember being in video village and feeling like, man, when the audience sees this, I don't know what they're going to feel. The performances are just amazing.


Issa Rae and Jay Ellis, Insecure


Molly and Andrew are the other couple on the verge of breaking up in the season finale. Despite the fact that it was a good relationship, will Molly's walls go back up in Season 5? Or will she learn to value people even if she has to let them go?
All I can say is you hope characters grow. And I think we're going to see some growth from Molly next season. I think how that manifests itself -- we always say it's two steps forward, one step back. But I think that that's a thing we want to explore with this character so it's more growth for sure.

This season really emphasized that Molly and Issa are the core relationship of the show. How did you approach this friend breakup in the writers' room to make it even more gutting than the romantic ups and downs on the show?
We tried to lean in on the fact that they have a history and the audience has been a part of that history. So a lot of the heavy lifting is done for us because you've been watching this show for three years and as a result, you know what these characters have gone through. They know where all the bodies are buried. We wanted to explore these characters who weren't maybe fully appreciating each other, maybe taking each other for granted.

What Issa and Molly had to realize is that these friendships don't come along every day. Just getting rid of each other because you're mad, you're hurting -- no matter how much you're hurting, you'd be losing something very special. That was always hard for us in the writers' room because we wanted to tear something apart to kind of piece it back together. We wanted to see, could the friendship survive? Each episode this season is a sort of paper cut; they know too much about each other and they're weaponizing it in a way that's not healthy because they're upset. That's some of the stuff we want to get into next season, we want to get back to where their history is used to build each other up, not to criticize and pass judgment. We didn't -- and don't -- want it to turn into a show about frenemies because that's not our show.

Insecure Boss Weighs in on the 'Unnecessary' Molly Backlash

Where do you see Molly and Issa's friendship heading in Season 5? 
I can't imagine a world where Issa and Molly don't love each other. I don't want to live in that world because that world feels very cold. We wanted to show that they were going to come back together and start to talk at the end of the finale -- and we'll see what happens from there. But there's no amount of scene length that could do justice in one episode in the last five minutes, that kind of like summed up what everybody's been feeling. So all we wanted to say, based on what happened with Tiffany and their friendship and all of it, the experience just put in perspective how fragile those relationships are and that they were taking a step in the right direction. They were both missing each other and that they need to take a step in the right direction.

I think it's about allowing each other space to grow. We want to see them get to make mistakes in each other's space and for those mistakes to not turn into giant consequences. Not holding their past against each other, but just letting each other exist and giving each other their space that they were asking for. The thing that we liked exploring this year, and will get into more next season, was this idea that they're just more self aware of their own flaws in the space and it's not just the other person's fault. 

Insecure Season 4 is now streaming on HBO.