Don’t Freak Out, but ‘Insecure’ Season 5 Will Dig Deep Into *That* Issa-Lawrence Reveal

Lauren Puckett
·4 min read
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Truly, is there anything as radiant as an Issa Rae grin? Television has felt noticeably less sunny since that smile went away when Insecure season 4 wrapped in June, leaving us with a lot of Issa-Molly baggage to sort through and, uh, so many questions. Like, will Issa and Lawrence stay together? How will Condola handle a literal infant? Will Nathan work his way back into Issa’s affections? And will Molly and Issa ever get over their “trauma bonding”? Thankfully, Rae and her fellow castmates loooove dropping little bread crumbs on social media for us fans to eat up, so here’s what we’ve gathered along the trail.

Insecure season 5 is a go, friends.

Only a few weeks into season 4, HBO dropped the big news that they’d ordered yet another season. Amy Gravitt, executive vice president of HBO Programming, said, “We’re thrilled that Issa, Prentice [Penny, producer], and the whole Insecure team will be getting back together for a fifth season. As we laugh and cringe with recognition, their stories make us all feel a little less alone in the world.”

But the release date is a big question mark.

In an interview, Rae hinted to Variety in May that Insecure might be back as soon as next year, given that filming is supposed to start back up in November. But this little thing called COVID-19 might derail all those sweet, simple plans. She told the outlet, “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.”

However, she did reveal that the writers were already hard at work, meeting virtually to discuss season 5 scripts. “It feels really good to be back,” she said. “And it’s like my only social interaction right now is just the weird virtual writer’s room. So that part is really exciting.”

Don’t expect the coronavirus to make a splash onscreen.

When asked whether the pandemic would be part of the season 5 story, Rae told Variety, “I already have fatigue of it because we’re living it and I think that’s my biggest worry is just, you know, I don’t want the show to feel dated, and obviously certain aspects will already feel dated by nature. I think there might be a world where we acknowledge it in the background, because I think it obviously will have long-lasting impacts."

In a more recent chat with Variety, when asked about Molly and Issa’s changing relationship ahead of next season, Rae replied, “Can’t talk about Molly & Issa 3.0 when this virus is still out there. Wear your mask, people, please—and vote.”

Issa and Lawrence’s future is up in the air.

Just as Lawrence was working his charm on Issa, making her dream about their future together, he had to turn around and find out that his ex Condola is pregnant with his baby. This changes Issa’s perfect vision, erm, just a bit! The finale ends without letting us know if Issa and Lawrence decide to stick it out together.

“It’s purposefully ambiguous, that that’s the moment we leave the scene,” Prentice told Entertainment Weekly. “The stuff we want to explore in season 5 is, what happens now?”

Molly will finally get to be happy. Maybe?

In an August interview with Variety, Yvonne Orji, who plays Molly, said she feels Molly and Issa’s relationship will enter a “3.0” stage. “I feel our relationship is ‘iron sharpens iron’—I feel like we’re sharpening each other as friends and even frenemies,” she said. “We’ve been circling around each other in just getting familiar with the old way of how we used to be. We’re all growing. And change is hard. I would like to see Molly happy, in general, just happy. In love and life, at work, I want her happy. Is that too much to ask?”

Oh, and don’t sleep on Nathan.

With the whole ~baby thing~ throwing an unexpected twist in Issa and Lawrence’s love, old flame Nathan might find a way to finagle his way back into Issa’s welcoming arms.

“I think we’re trying one of the questions that’s still sort of hanging from this: The Issa-Lawrence Issa-Nathan [relationships],” Penny told EW. “Really, the thing we’re playing with is, again, if life doesn’t look like how you imagined it, does that mean it’s a success or a failure?”

Either way, as long as we get that Issa grin back on our screens again, we’ll be okay, okay?

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