An Insecure Retrospective
It’s finally here.
I am a huge fan of HBO’s Insecure and have been thinking about this moment for over a year. Waiting for this moment for weeks. The first episode of the last season of Issa Rae’s 11-time Emmy nominated series airs tonight. I am excited to see a new episode of the show, but I know I’m gonna cry through the season watching all these beautiful storylines come to a close. It’s definitely bittersweet.
To celebrate and to make the most of this last season, I want to write out what my predictions are. The show has covered a LOT of ground in four seasons. Black male sexual fluidity in the character of Jared. Black male depression through season one Lawrence. Issa as the forever struggle friend who doesn’t get herself together until the end of season three. Open relationships. (Dro. … Chile!) Mental health and all the ways we manage and mismanage it through the characters of Nathan and Molly. Issa, Lawrence, and Molly all glowing up in their careers. Derek and Tiffany (and, now, Lawrence and Condola) becoming parents. And, most importantly, how all these momentous late 20s and early 30s life changes disrupt your relationships. There’s so much to unpack and I am sure that I will be talking about and re-watching this show for YEARS.
The writers of Insecure have been excellent at giving us hints at what’s to come for the entire series. In preparation for tonight’s premiere, I spent the last week re-watching the series, and based on some semi-educated guesses, this is what I think is going to happen.
Somebody’s Gonna Die
These characters have gone through everything you go through in your 20s and 30s except dealing with the death of a loved one, specifically the death of a parent. By your early 30s, many, many people lose a parent. Or, they know someone who has. It’s pretty surprising that none of the main characters have experienced that loss yet. In season four episode 9, Issa calls her brother, Ahmal, for advice and the first thing out of his mouth is, “Stanley, dead?” While there’s no guarantee that their mom’s boyfriend Stanley will actually die, I think somebody’s mom or dad will.
Molly Finally Gets Real
We saw the moment in season four episode 7 when Molly calls Dr. Rhonda from the beach in Mexico. While she does later have a session in which Dr. Rhonda poses the question, “Do you want to be right or do you want to be in relationships?” Molly chose the former over the latter and all but ended her friendship with Issa in episode 9. Then, in episode 10 we see Andrew breaking up with her and Molly being completely caught off guard when he asks, “What are you really fighting for?” It’s fascinating how easy it was for Molly to label Issa as selfish, but she can’t see the same career-obsessed selfishness in herself. All that said, if the natural hair Molly is rockin’ in the trailers is any indicator (after SERV.ING. US. with these wigs. For years!), I expect to see Molly go through some massive changes in this final season.
Molly Ends Up with Taurean (Yes! More on Molly!)
Since Molly transitioned to her current law firm in season 3, her coworker,Taurean has been a persistent presence due to his dominant performance in the office. On their brunch date in episode 9, Issa mentions in passing that Taurean came up on her Instagram. I’ve long thought that Taurean would make the best match for Molly. He works hard and is just as driven as Molly is, but we also know from Issa’s mention of him on IG that he knows how to play hard too. Molly lacks that skill. And, let’s not forget the moment in season three when Taurean switched cases instead of co-leading with Molly. Taurean is about his business, but business isn’t all there is to him. Molly doesn’t have that quality, but Taurean could be the one to teach her. And, maybe, it could turn into something more.
Lawrence is Gonna Be a Good Dad
To everyone’s great sadness, it is confirmed that Lawrence and Condola will be co-parenting a child together. There’s just no getting around it. (But, honestly? How sway?!? Lawrence screwed everything walking for two seasons and got chlamydia doing it, but now he has weak-ass pull out game? Condola is the most put-together of put-together people so much so that she organizes everything for everyone else. … But, she’s not on any form of birth control? Seriously?!?!? Make it make sense.) In season four episode 4, we see Kelli say, “Look at Lawrence over there. Looking like a provider.” Now, with his new job in San Francisco he has the ability to do that. Is this the way that any of us wanted Lawrence to finally step up? Of course not. Is he gonna do it though? Yep. Issa said it herself. Lawrence isn’t a sometime-y dude. [shrug] I guess dad jokes are going to be called Lawrences now.
Issa is Team Nanceford
I want to state for the record right now that as much as I love the pure romance that is Issa and Lawrence, I hope Issa ends up with Nathan. Nathan is the only person that believed in Issa when she didn’t believe in herself. He’s the only person that is honest and vulnerable with her without the relationship having to break first. Nathan’s the only person that not only hears and sees Issa rapping to herself, he amps her up and raps with her. And, probably, most importantly, he’s the only person that she didn’t have to build up.
Issa had to build Lawrence while he was depressed and unemployed for 2 years in their Dunes apartment. She cheered Molly on in her relentless quest for partner at her various law firms. She helped Daniel meet Spyder at the club so maybe he could finally get his big break as a music producer. Issa, for years, didn’t know how to fix her own life, but she was there for everyone else’s. But, the moment she cleaned up her life, who was there? Nathan. And,he was fully supportive of her from day one. On top of that, Nathan is the only person Issa has gotten to be her best, post-We-Got-Y’all self with. It took Issa so long to get to healthy and happy. I want her to stay there, and I believe Nathan is the best (read: “healthiest”) person for the job.
Or Issa is Solo Dolo
Alternatively, if Issa ends up 100% single but a bomb-ass entrepreneur, I will be down with that too. We learned at the end of season three (and in episodes 6 and 9 of season four) that even when it gets rocky, Issa can make it on her own. I’d be equally happy to see her walk into the LA sunset standing completely on her own two feet.
I have other theories that are less well thought out:
- Maybe Molly will sing the “You’re My Best Friend” song back to Issa.
- Maybe Ahmal and Kelli will actually get along for 10 minutes.
- Maybe Tiffany was a surrogate and Simone is actually Kelli’s daughter.
If you’re wondering, no I didn’t forget about the biggest plot point which is whether or not Issa and Molly will heal their friendship. But, I read an article once where Prentice Penny (Insecure’s showrunner) defined the love story of the show as being Issa and Molly’s friendship. I don’t know how they’ll work it out, but I know that they will.
Still, I’m sad to see them go. Issa Dee is my friend in my head. (She’s me but better to be honest.) I miss her and the whole crew already. And, I am so thankful and proud of Issa Rae for creating these characters, this show, this world for the culture. Here’s to the end of a beautiful ride.