'Insecure' Showrunner Prentice Penny Breaks Down the Season 5 Premiere (Exclusive) 

Insecure Season 5

On Sunday, Insecure returned with its fifth and final season as it begins to close out its story about Issa (played by co-creator and star Issa Rae) and her best friend, Molly (Yvonne Orji), navigating the ups and downs of adulting in Los Angeles. And for every step forward, there’s always a few steps back, especially seen in the season 4 finale, which left Issa facing difficult decisions to make when it comes to her career, her love life -- in this case, with Lawrence (Jay Ellis) -- and friendship.  

During a conversation with ET, showrunner Prentice Penny explained why the season 5 premiere saw Issa and her friends, including Kelli (Natasha Rothwell) and Tiffany (Amanda Seales), returning to where things all began, how key decisions will affect the rest of the season and why there isn’t a show within a show this year.  

[Warning: Spoilers for Insecure season 5, episode 1, “Reunited, Okay?!”] 

“Last season, obviously there was a lot of turmoil in Issa and Molly’s lives, collectively and individually. So, coming off of that, we were trying to build on this idea that we can’t always control the cards you're dealt. It’s really how you play them,” Penny says, setting up the driving concept for season 5.  

“And so, the theme for us was, ‘Am I going to be okay if... fill in the blank.’ Like, Am I going to be okay if I’m in love with Lawrence but it looks different than how I thought? Am I going to be okay if Molly and I don’t get back on track? Am I going to be okay in my career if things don't go a certain way?” he continues, adding that “the same goes for Molly. The whole thing was trying to answer that question for all our characters.”  

Insecure Season 5

With that said, the premiere opens a few months after the finale as Issa, Molly, Kelli, Tiffany and her husband, Derek (Wade Allain-Marcus), reunite at Stanford for a 15-year anniversary. Of course, things don’t go as planned as Molly is still reeling from her breakup with Andrew (Alexander Hodge) and navigating tense-filled interactions with Issa, who finds herself losing confidence in her own community-based business, The Blocc. Elsewhere, Kelli finds out the university thinks she’s dead and has included her in its in-memoriam programming.  

Returning to Stanford was an important decision for the show and to see how Issa and Molly can move forward. “We always wanted to go back to the birthplace of their friendship and kind of examine why they were friends. And then, almost them needing to remember why they were friends,” Penny explains, noting that the two are not really back to where they were before. “They are still on eggshells.” 

And so, for most of the episode, they are testing the waters with each other, with Molly asking Issa, “Are we going to be okay?” In the moment, Issa doesn’t answer the question directly, but is seemingly interested in making things right. “We were trying to show that Issa and Molly are cool, but are they cool, cool?” Penny adds.  

Later, the four women and one of their former Stanford friends, Cheyenne (Taja V. Simpson), decide to head out to a party when Issa, Molly and Cheyenne get stood up at a convenience store and it’s revealed that Cheyenne is behind the theft. While scary at first, it becomes a laughable moment that breaks the tension between Issa and Molly. 

“They’re like a Lucy and Ethel in the way they always find themselves in these weird, crazy situations,” Penny says. “And because the tension is so thick, you just have to laugh about it. And them giving each other crap was a fun way to show that they’re back... They needed something to laugh at that wasn’t at anybody else’s expense. And it was a reminder that these are the kind of moments these friends get in. They’re just special together.”  

Insecure Season 5

While that moment brings Issa and Molly back together, Kelli is still upset about her premature death. And that’s something that’s going to be a driver for her the rest of the season. “We always want to dive more into Kelli, but we just don’t always have the screen time to do it,” Penny says, noting that after what they saw of Rothwell’s performance in season 3, when Kelli feels left out while Tiffany is pregnant, they knew they wanted to revisit that vulnerability once more.  

So, when it comes to her death, “we wanted this moment not to just be a joke, right?” Penny says, explaining that Issa, Molly and Tiffany’s fake memorial service isn’t just for laughs. “That has a real impact on her. To be remembered and your legacy, what you’ve left behind. So, that’s a big thing for the character this season.”  

That subplot is also capped off with Kelli returning home to record her podcast. And given the series’ history of including a show within a show, it remained to be seen if this season’s installment was going to be meta as Kelli narrates her life. However, sadly, that’s not the case.  

The podcast, it turns out, is a reference to a joke made in season 1, while Insecure had to scrap the show within a show concept in season 5 due to filming amid COVID-19 restrictions. “We had a couple ideas,” Penny says. “But nothing really came together and with the COVID protocols, it was just too much by the end. And so, this will be the season that there isn’t a show within a show.”  

Insecure Season 5

While that’s a disappointing revelation, it’s not as sad or as shocking as the final moments of the premiere, when Lawrence picks up Issa from the airport. And after the two return home, Issa ends things, telling him she had a chance to think... As to whether she’s specifically ending things over Lawrence’s move to San Francisco or the fact that he has a baby with Condola (Christina Elmore) on the way is anyone’s guess.  

“She’s making grown-up choices,” Penny says. “And so, it’s like, ‘What are the things that are most important to her right now?’ And the things that are the most important are obviously her career, which is a thing she wants to make sure is taken care of, and her friendship with Molly. That’s where her energies can be right now.”   

He adds, “I think that’s a real growth moment for Issa, just to say, I can’t.” 

And with Lawrence seemingly out of the picture, it may make Nathan’s (Kendrick Sampson) return more significant. “Last year, he made Issa think that he still had feelings for her, even though that wasn’t a possibility,” Penny says. “But he’s single now, so we’ll have to see what happens.” 

Insecure airs Sundays at 10 p.m. ET/PT on HBO. Want to watch more? The entire series is now streaming on HBO Max. (We may receive an affiliate commission if you subscribe to a service through our links.)

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