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What To Remember Before Watching Insecure Season 5

We've known since January that "Insecure" Season 5 would be its final season. The announcement has left fans of the HBO dramedy mentally and emotionally preparing for the final act of Issa Dee (Issa Rae) after four eventful seasons. What is next for the unsure-of-herself twenty-something protagonist we met in the 2016 series premiere? And what are we going to do in a world without Molly (Yvonne Orji), Lawrence (Jay Ellis), Nathan (Kendrick Sampson), Kelli (Natasha Rothwell), and Tiffany (Amanda Seales)?

Season 4 took a very adult approach to the story and explored some pretty rough topics. Molly tried her best to make room for a serious relationship in her life and hit more than a few bumps in the road. Tiffany struggled with postpartum depression that, in the end, brought her and Derek closer together. Kelli remained reliable and supportive of Issa and Molly as the two friends weathered a rough patch. Looking forward, we can expect these many plot threads to find some real closure in Season 5.

If you're just now getting into this gem of a show or need to refresh your memory on what happened the last time "Insecure" was on the air, you're in the right place. Let's refresh on the major plot points and cliffhangers that the showrunners have let linger since the Season 4 finale aired in June 2020.

Issa and Lawrence dealt with shocking pregnancy news

In the Season 4 finale, the newly-rekindled romance between Lawrence and Issa gets a massive wrench thrown into it. Condola (Christina Elmore), the woman Lawrence dates for the majority of the season and the same person Issa works with on her game-changing block party, is pregnant (via Black Girl Nerds). Condola and Lawrence split as it becomes clear they've drifted apart — which conveniently occurs right around the time he and Issa give their relationship another shot. What complicates matters further is the fact that Condola wants kids. Though her current situation isn't ideal, she starts on her pregnancy journey under these imperfect circumstances rather than risk waiting too long for the "right time" and miss out on motherhood altogether.

Condola appears easygoing about everything — so far, anyway. She even tells Lawrence that he can be "as involved as he wants to be" in the baby's life, which is a polite way of saying, "I can raise this baby on my own. I don't need you." He wants to do right by his child, but he also wants to be with Issa. 

In the end, Issa and Lawrence's future appears to be in limbo after the pair speak about his move up to San Francisco and realistically explore what it would mean for them both. It's a lot for Issa to deal with all at once, and her future with her old flame is in limbo at the close of Season 4.

Issa's professional future is wide open

One of the overarching plot points for Season 4 is the big block party Issa organizes for her neighborhood. This huge endeavor spurs several subplots, including her reunion with her ex-boyfriend, Lawrence, and the beginning of some serious problems with her bestie Molly (via Entertainment Tonight). Season 5 will start with Issa riding high on her recent professional success — but to what end?

The official trailer for the upcoming season (via YouTube) may bum fans out a bit. One of the primary arcs throughout the HBO series is Issa's perpetual search for professional stability and success. She appears to be coming into her own in the regard in the most recent season. But the trailer pivots from Issa's block party success to her suddenly floundering in a sea of potential opportunity. 

It's easy to see why the writers would do this. A season full of Issa going straight from one success to another would be unrealistic and potentially boring. But setting her up to fail, followed by triumph, or a bittersweet struggle that fails to yield any dividends would make a compelling end to a compelling series.

Molly and Issa take the first steps toward rekindling their friendship

At the end of "Insecure" Season 4, Molly and Issa meet up at their favorite restaurant and finally hash out their issues. Over the course of the season, the audience bore witness to the emotional turmoil which accompanies two best friends drifting apart. For most of the season, Issa finds success in both work and love, but Molly is stuck in a relationship rut with Andrew (Alexander Hodge) and hits the skids at work. It's a first for the relationship dynamic to switch for the two, and neither woman handles it well. A lack of communication and good conflict resolution skills only exacerbates the situation, ultimately creating a rift between them.

Molly and Issa have their pivotal reconciliation chat offscreen, which means we still don't know what exactly came out during the long talk. If we consider the Season 5 trailer, it looks as though a big overarching plotline revolves around the two of them building their friendship back stronger following this conversation. However, we won't know exactly what the deal is with these friends until we watch the first episode of the final season.

The "Insecure" Season 5 opener debuts Sunday, October 24 on HBO at 9 p.m. ET. The first episode will also be available to stream on HBO Max following its HBO release.