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‘Insecure’ Season 4 Air Date: Fourth Installment Expected to be Series’ Most Complicated Yet

“Insecure” Season 4 is expected to be even messier and chaotic as relationships get tangle up and explored. Issa (Issa Rae) and Molly (Yvonne Orji) are seriously looking into building a foundation with roommates Nathan (Kendrick Sampson) and Andrew (Alexander Hodge).

It goes without saying that dating people in your circle almost always ends up getting complicated as subjects that were easy to broach before becomes land mines when romance is involved. Speaking with The New York Times, Rae provided a bit of hint where “Insecure” Season 4 is headed.

“I always called Season 3 the set-up season,” Rae said. “We were having to get all our characters to this place where they have to face each other and face themselves. There’s that point in your life where you question everything around you — where you’re like, I’m at this certain age. Do I need to make the effort to make this career or these relationships last? Like, where and who do I want to be? And that’s something we’re going to home in on.” It would seem that confusion and personal journey will be highlighted in “Insecure” Season 4 yet again.

Regarding the final installment for the dramedy, Rae said that she has an idea of how to wrap everything up. However, she did admit that she’s having trouble tying loose threads together and is currently working on how to provide a satisfying conclusion to Issa and Molly’s story. This is especially true since “Insecure” Season 4 will be a problematic plotline, Refinery29 reported.

Aside from Issa and Molly’s new relationship, another complication has popped up in the horizon. The issue in question is Condola (Christine Elmore). It’s already been established that Condola and Lawrence (Jay Ellis) – Issa’s most significant ex – will be an item in “Insecure” Season 4. This wouldn’t be that much of an issue if not for Issa eyeing Condola as a serious business partner. As for when the fourth installment will be released, Rae said that it won’t be coming out anytime soon.

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