‘Insecure’: What Happens When Your 'Work in Progress' Ex Levels Up?

insecure issa and lawrence

It’s probably best to start by saying I HATED Lawrence in the first season of Insecure.

He was the sort of “nice guy” that shouldn’t get a free pass, but too often does. He was one of the few mainstream black characters that comes from a solidly middle-class background. The nerdy black guy that has nothing to do with gangs, drugs, or athletics that TV often pretends doesn’t actually exist.

But take that away and all that’s left is an unemployed, unambitious man who totally took Issa for granted. It may have been a temporary state, but when we first met him, he was a total bum and there was no getting around it. It was definitely a big factor in the demise of their relationship and, even though it was wrong she cheated on him, it was the push they both needed to get out of a toxic dynamic.

insecure issa lawrence
Issa and Lawrence, season 1

Post-break up Lawrence has gotten his shit together. He’s also back in Issa’s life since her business partner turned out to be Lawrence’s new girlfriend. And even though I am happy for him, Issa definitely got the short end of the breakup.

In one episode, Issa laments that “she got the work in progress” while his new girlfriend gets to date the man Issa was waiting for him to be. My heart broke for her because it is totally true. In a weird way, Lawrence gets to live out the life that Issa was trying to build for them without her. Lawrence 2.0 is actually putting effort into his personal and professional life, working at a startup he’s interested in and wining and dining a woman who Issa aspires to be.

Meanwhile, the woman who emotionally supported him, covered their bills, and refused to give up on him (aka Issa) doesn’t get to reap the benefits of being a supportive partner for 5 years and is basically having to start over. As Insecure creator Issa Rae explained,

“You can think that you’re over someone, and you can still be over someone, and still feel like, ‘Man, I made you better. I made you better for the next b**ch, and I’m not even going to get any credit for that.'”

insecure season 4 review
Lawrence and his new girlfriend Condola, season 4

The fact that Issa stayed for as long as she did is remarkable and speaks to the burden that women often take on for their partners. Sure there was love and comfort that kept her in the relationship, but she also had a sense of duty to help him achieve his best.

This idea of “sticking by your man” is particularly fraught for black women. There’s a sense that, since society beats down black men, we should be there to encourage them and should be slow to criticize them. (Tyler Perry has made a career out of movies that chide successful black women for looking for their equals).

It’s messaging that is even on Insecure itself. Molly may lack people skills and be a little clueless in relationships, but more than once, Issa has implied that her romantic failures are a direct result of her high standards and desire to “fix” her boyfriends.

Issa has a lot of emotional frustration to unpack. From the outside, Lawrence is doing well and it proves that her faith in his potential wasn’t misplaced. He was just too complacent to realize that potential while they were in a relationship.

In the end, he was a terrible boyfriend and she shouldn’t regret they ended when they did (although I doubt she’s proud of how it ended). But it’s hard not to mourn what could’ve been. Even if they are both better off, I can’t stand the feeling of watching the mediocre partner “win”.

Insecure airs on Sundays on HBO.


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Ayo Osobamiro
Ayo is a writer and producer based in Brooklyn, but proudly from the Midwest. When she's not agonizng over applying to grad school, she is working on her first podcast, I Think I Read This Somewhere