Insecure Season 5 - What We Know So Far

Insecure, created by Issa Rae and Larry Wilmore, became one of HBO's best and most beloved shows soon after its debut in 2016. Exploring the Black female experience in Los Angeles through the eyes of friends Issa (Rae) and Molly (Yvonne Orji), the show has become a major awards contender, with the most recent season earning eight Emmy nominations, including one for Best Comedy Series.

In the fourth season, Issa and Molly were on the outs after having a major falling out in the season premiere. This rift changed the dynamic of the show, and some fans were worried it might be too much for the show to handle. Luckily that wasn't the case, as the season was well-received by fans and critics alike. Meanwhile, the two friends eventually sat down to reconcile and talk about their issues at the end of the season. But that wasn't all that happened. In the game-changing finale, Lawrence (Jay Ellis) also revealed that his ex-girlfriend Condola (Christina Elmore) was pregnant with his child, a development that obviously threw a wrench into Issa's life.

When the popular HBO series returns for its fifth season, it will have to deal with all of this and more. Here's everything we know so far about what to expect from season 5.

HBO renewed Insecure for a fifth season in May 2020 just a few weeks into the acclaimed comedy's fourth season. It was later confirmed in January 2021 that season 5 would be the show's last. Issa Rae, in speaking with Deadline, said that she and showrunner Prentice Penny had "always planned to tell this story through five seasons," but acknowledged that it wouldn't have been possible without the support of the show's audience. "I feel blessed beyond measure to bring our characters' stories to an end, on-screen at least," she said.

At the same time HBO revealed Insecure would end with season 5, it also announced that the series was returning to production in late January and was slated to debut later in 2021, though an exact date has not yet been set. We also don't yet have an episode count for season 5. The first three seasons ran for eight episodes each, but season 4 was bumped up to 10 episodes, so it's anybody's guess right now.

HBO has not yet announced or confirmed who will be returning for Insecure's fifth and final season, but it should go without saying that series creator and star Issa Rae will return as Issa Dee to finish out the show's run. And you can bet money on Yvonne Orji returning as Molly and Jay Ellis returning as Lawrence. You might even see Kendrick Sampson return as Issa's ex Nathan since executive producer Prentice Penny previously told Entertainment Weekly that the Issa-Nathan relationship is one of the questions that is still hanging after the events of season 4. Well, that and the actor was spotted on set already, per Popsugar.

Elsewhere, you should expect Natasha Rothwell to return as Kelli and Amanda Seales to reprise her role as Tiffany. And while this is just speculation at this point, given the bombshell that ended the fourth season, it would make a lot of sense for Christina Elmore to also return as Condola.

Any new cast members will be announced at a later date.

The final season of Insecure will continue to follow Issa and her friends as they evaluate their relationships, both new and old. This means dealing with the events of the end of the season, which saw Issa and Molly come back together after a season apart. According to executive producer Prentice Penny, fans shouldn't expect the two women to just act like nothing happened though. "They're going to be forever changed by this, forever humbled by this, and hopefully, forever close by this," Penny told Entertainment Weekly. "I don't think it's about getting them back to where they were. I think we're always going to have a version of them having fun together because they're friends, but I think we want to explore what is that road back like and how is that road different."

Elsewhere, Lawrence dropped the bombshell his ex was pregnant. The writers left the outcome of that discussion and whether Issa and Lawrence broke up as a result of the news purposefully ambiguous, so you should expect season 5 to deal with the fallout of that as well.

Another possible storyline you may see in season 5 revolves around the pandemic. In May 2020, shortly after the show was renewed, Rae spoke to Variety about writing the fifth season and was asked if COVID-19 would play a role. While she couldn't say for sure since the writers' room had just reconvened, it is definitely possible. "I think there might be a world where we acknowledge it in the background," Rae told the trade, "because I think it obviously will have long-lasting impacts."

If COVID-19 does make it into the final season, it seems likely the show will address its impact on the Black community. In the same interview, Rae pointed out many of her favorite restaurants and Black-owned businesses in South L.A. were forced to close and said she didn't want to appear tone-deaf by ignoring what has happened. "We've always taken pride in representing the city as is," she said.