Everything We Know About 'Insecure' Season 5

The Issa Rae comedy is coming back for another season.

Yvonne Orji and Issa Rae | Merie W. Wallace/HBO
Yvonne Orji and Issa Rae | Merie W. Wallace/HBO

It was just back in 2016 that Issa Rae took her talents over to HBO to adapt her popular web series Awkward Black Girl into Insecure. Now, after four successful seasons and 11 Emmy nominations, the comedy has become a mainstay and the hype around it only (rightfully) continues to grow. Following a young Black woman in LA named Issa Dee and her (mis)adventures in professional success, friendship, and love, the series co-created by Rae and Larry Wilmore has been hailed for its relatability and earnest laughs -- and has drawn seriously divided lines between fans about their eye candy of choice. 

While Season 4 saw Issa and her BFF Molly (Yvonne Orji) trying to "level-up" in their personal lives, it seems like the two still have a long way to go on their own, and as a duo. Considering the season finale seemingly left many things unsaid and dropped a handful of bombshells, it's definitely fair to start looking toward the next installment to see how everything gets patched up. While we'll have to kill time with some mirror raps of our own as we wait for more of Issa's, here's everything we know about Season 5 of Insecure so far. 

Will there be a Season 5 of Insecure

No need to freak out: Insecure is definitely coming back for a fifth season. The renewal was confirmed before Season 4 was even over, back in May 2020, as reported by Deadline. They shared that showrunners "Issa Rae, Prentice [Penny], and the whole Insecure team will be getting back together," so it should be another round of laughs and tears as usual. 

When will Insecure Season 5 premiere? 

So, the good news is that Season 5 appears to at least be written, but the bad news is, it's impossible to say if the series will be able to follow through with its current production schedule. In early May, showrunner/star Issa Rae shared on Instagram that she and her writing team, including executive producer Prentice Penny and co-star/writer/producer Natasha Rothwell, were back at it, remotely writing Season 5. While it's good to know that by now the show is likely ready to go for the upcoming season, Rae shared with Variety that they hope to get into production in the fall, but they can't say whether or not that will actually happen. Rae said, "Obviously we have a schedule where we're supposed to shoot, but who knows if we're going to meet that. Who knows if we're even going to be able to come out next year, so there's just so many 'if' factors."

If all goes well, considering their current plan, a spring release similar to Season 4 seems like a possibility for Season 5. But on the flip side, if the cast and crew can't get back to set when they're hoping to, that could push the release back to late 2021 or -- unfortunately, like Issa said -- early 2022. Insecure fans will remember the painful wait of a year and a half between Seasons 3 and 4, and even though the series showrunners don't want to put fans through that again, at least we're used to waiting for more from Issa and co. 

Who in the cast is returning?

Insecure wouldn't be the same without its core cast, so you can assume that all of the main leads will be back. Issa Rae will most definitely reprise her role as Issa Dee, Yvonne Orji should be back as Molly, as well as Natasha Rothwell as Kelli, Jay Ellis as Lawrence, and Amanda Seales as Tiffany. 

Now that Andrew (Alexander Hodge) and Molly broke up, though, it's hard to say if we'll be seeing any more of Asian bae. But as for Condola (Christina Elmore), it seems like she'll definitely be sticking around, given the news she dropped in the season finale. More on that reveal below, but when you consider the detour that throws in Issa's relationship with Lawrence, it might be time for Nathan (Kendrick Sampson) hive to shine and for that ex to be back in the picture as well. 

Jay Ellis and Issa Rae | Merie W. Wallace/HBO

What will the new season be about? 

According to showrunner Prentice Penny, the upcoming season hinges on one question: "If life doesn't look like how you imagined it, does that mean it's a success or a failure?" He spoke to Entertainment Weekly about what that means and how it should carry into Season 5, and it builds upon just about every one of the developments from that jaw-dropping finale. 

Like, while Issa and Molly attempted to talk things out after their relationship took a hit when they each tried to focus on their own lives, their friendship isn't necessarily going to be back to normal. Penny said, "We don’t want them to go back to where they were. They’re going to be forever changed by this, forever humbled by this, and hopefully, forever close by this." He explained that the new episodes will explore what the road back to their close friendship, and ultimately the "2.0 version" of it, will look like. 

Where their relationship stands isn't the only unpredictable wrench thrown into Issa's life that'll be explored going forward, though. Penny explained to EW that it was intentionally left uncertain whether or not Issa and Lawrence are still an item, but now that Condola is pregnant with his child, Issa will have to reevaluate whether or not she still wants a life with him even if it's not the idealistic one she imagined. Could that send her back onto the Nathan train? It's hard to say, but it'll certainly affect Lawrence individually, and whatever relationship remains between the two of them. 

It sounds like all of that drama, on top of Issa's continued professional pursuits and Molly's own dating struggles, should largely shape the next season. Continue to check back, though, as we'll continue to update this post as more information regarding what's up with our favorite LA friends we wish we were friends with is announced.

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Sadie Bell is the entertainment editorial assistant at Thrillist. She's on Twitter at @mssadiebell.