‘Insecure’ Finale: How Will Issa Handle That Lawrence Bombshell? (RECAP)

Insecure finale - Issa Rae and Jay Ellis
Spoiler Alert

[Warning: The below contains MAJOR spoilers for the Season 4 finale of Insecure, “Lowkey Lost.”]

Things seemed be going right for Issa Dee (Issa Rae) going into the fourth season finale of HBO’s Insecure, but we all should’ve known the other shoe was about to drop… and then it did.

Backing up, this whole “low-key” season has been a series of highs and lows for our mirror-talking protagonist. The high for Issa being the block party she’s been trying to get off the ground since Season 3, which was a huge success and a good sign that her shaky professional life was finally on track.

The lows — and yes, there were multiple lows — fell in the area of Issa’s messy personal life. First, her relationship with BFF Molly (Yvonne Orji) hit a rough patch when the two fell out sync for reasons that weren’t clear to either one of them (yet seemed so realistic to anyone who’s ever drifted from a close friend). But things grew even worse when Issa, in an effort to get the block party to be as lit as possible, went around Molly and asked her new music industry boyfriend, Andrew (Alexander Hodge), for help, which resulted in a major blowout. Since then, the friends have been trying to get back on the same page without success.

Also both exciting and nerve-wracking to watch was Issa reconnecting with ex Lawrence (Jay Ellis) and the two eventually getting back together. However, she’s also been spending time with another former beau, Nathan (Kendrick Sampson), whom she’d thought ghosted her last season. As she found out in this season’s penultimate episode, he wasn’t just another dog of a man but was actually dealing with being diagnosed as bipolar and learning to handle his bouts of depression.

It almost looked like we were heading into a season finale love triangle with Issa having to decide between the two men, but, come on, you should never sell Insecure short. This show is way smarter than falling back on that old storyline trope!

At the start of the season ender, Issa found out Lawrence got his dream job in San Francisco. And while he’s concerned about how she’ll react, given that their relationship is currently in a very good place, she’s refreshingly happy for him. They even talk about her eventually moving up to San Fran, assuming things continue to go well in their relationship. But what about Nathan? He’s expressed his feelings for Issa but she nipped that in the bud when she chose Lawrence, and Nathan is surprisingly chill about her choice. Issa seems to have her romantic life under control — though remember that other shoe that’s set to drop? It’s coming…

But first we move over to spend time with Molly and her own relationship woes that come out with Andrew, who lets her know that he’s tired of always doing what she wants and his wants and desires taking a backseat. He later tells her that maybe they’re just not right for each other and, for once, Molly doesn’t have a quick retort for him. Sadly, she’s without her bestie to go to for advice and some sympathy.

There’s also friend drama in the finale with overwhelmed new Mom Tiffany (Amanda Seales) running off and leaving husband Derek (Wade Allain-Marcus) and the friends in a frantic search for her around downtown Los Angeles. You’d think the search might bring Molly and Issa back together, but that doesn’t really happen. Side note, while it did feel a little odd to spend so much time in the episode on Tiffany/Derek drama, since they haven’t been prominently featured this season, this does show that all the friends have grown since the first season and provides Molly and Issa a way to spend time together without leaning into the rift. (Nice job, executive producer Prentice Penny, who both wrote and directed the finale.)

And just as Tiffany is found OK and she reunites with Derek, we find the group in an unexpected confrontation with cops in downtown L.A., which brings a dose of reality into the show. It almost looks like we’re going to go down a road that mirrors what’s currently being addressed in society about how law enforcement treats black citizens. But, before things can get too intense — which they often do when Kelli (Natasha Rothwell) lets her mouth go — the situation diffuses itself without major incident. Still, it’s a reminder that Insecure isn’t just a comedy but a comedy that rests on a foundation of what’s going on in the real world, especially in Los Angeles.

Finally, it’s time for that other shoe to drop and it’s one hell of a bombshell! Lawrence comes over to Issa’s and tells her his ex-girlfriend Condola (Christina Elmore) has told him she’s pregnant and keeping the baby. (Yes, she also said in quick flashes to that conversation that she’s sure it’s Lawrence’s, and Condola has never seemed shady enough to lie about something like that, right?).

So what does this mean for Lawrence and Issa? He says he’s not going to get back together with Condola but the reality is that he’s going to be a father and that’s a lot for Issa to handle. The episode seems to be wrapping up with Issa sitting outside, smoking a joint and just contemplating everything all by herself… but that’s still not the end.

It’s perfectly fitting that the final scene in the episode has Issa showing up at her fave Ethiopian restaurant to meet up with… Molly! It’s truly the perfect way to both get their friendship back on track at a moment when they just need each other and to let everything else fall to the wayside for now. And, like the show and all of its characters, this whole season of Insecure has been an exercise in growth for all the characters. And, it also did what a season finale should do — leave you dying to get into the next season. Bring it, Issa!

Insecure, Season 5 Premiere, TBD, HBO