The fifth and final season of Insecure finally made its way back to our small screens on Sunday and like most of you, we were glued to our television and laptop screens to see how our fave fab four friend group, namely Issa Dee (Issa Rae), Molly Carter (Yvonne Orji), Kelli Prenny (Natasha Rothwell), and Tiffany Dubois (Amanda Seales), are all moving and grooving ahead after the events of season four. And by we, I mean Very Smart Brothas co-founder and Senior Editor Panama Jackson and, well, me, Contributing Freelance Writer Shanelle Genai.
Suggested Reading
Due to the fact that we both love this show and love to argue with each other (even though I’m right the majority of the time, no matter what Panama says), we decided to put our differences aside and mash our musings together for a fun column we’d like to call Insecure Intermissions. Every Monday, you’ll get a recap (of sorts) from us both where we’ll highlight some of our favorite moments from each episode and other random, yet applicable thoughts to the show’s cultural impact. So without further ado...
Insecure Intermissions
Panama Jackson: Whew, chillay! Insecure is byke and I couldn’t be more excited. And I mean that with my whole heart. My heart also gently weeps as I know this is the last season, which makes sense. Issa Rae has leveled up so much that any time I hear a song with the words “new level” I automatically think of her. She is literally the definition of “goals.” I’m proud of her like she’s my actual family. So yeah, sads. But happy sads. It was so exciting seeing the crew as they headed to Stanford for an alumni event and to watch Issa go all ABG on stage.
I have a bunch of questions heading into this season; here are a few: Is Molly still gon’ Molly? I’m definitely 2/10 stars, do not recommend on Molly. What’s up with le bébé and Lawrence? How is the Lawrence Hive doing? Can Kelli (RIP) get a spinoff??? (True story: I will NEVER forget her whole “REMEMBER ME DIFFERENT!!!”) scene from a few seasons ago—THAT was peak Black television. What’s up with all the dudes in Insecure and how do we wrap their storylines? I hate to see them leave but love to watch them go, ya know? What are your big picture initial thoughts on this last season?
Shanelle Genai: I think, as big of a mammoth as this show is, this season has to tie a pretty bow around everyone and the trajectory of their lives. And by “pretty,” I mean “somewhat fulfilling” because as we all know, Insecure never really gives us what we want, but what we need. And by “what we need,” I mean a very messy yet relatable AF look at a group of folks who’re literally just trying to figure this life thing out. I mean, can we talk about that moment Issa was speaking on that alumni panel and admitted to basically being unsure of whether or not she was on the right path as it relates to her new business/non-profit? If that isn’t “adulting” in a nutshell, I don’t know what is.
As far as the rest of the crew, I’m ready to see Molly get a grip on her relationship woes and learn how to be present in her friendships. When it comes to Kelli, I really hope they explore more on her “Prenny’s Preguntas” podcast because what a fire-ass name for a podcast. It’s also a cute callback to season one where she briefly mentioned she had a podcast in Malibu. As far as Tiffany and Derek go, I just have one question (read: a couple, actually) that needs to be answered by the time this show says so long: IS THE BABY REALLY DEREK’S AND WHO TF IS “FRED?”
Speaking of babies, though, Issa broke up with Lawrence because of his soon-to-be fresh out the womb baggage. Do you think there’s hope for them to get back together? Should we even hope for them to get back together, at this point?
Panama Jackson: You know, I really don’t think Kelli gets enough credit for her realness. Her whole statement about being “fake back” before being “back back” is some relatable content like a motherfucker, OKAY!? I don’t like Molly like I know her in real life so even her attempts to get “back back” feel super selfish, OKAY!? Also, I hope you see what I did there...twice. And I put it in caps so you know it’s real. Also, how hilarious is it of a brief storyline where you come back for an alumni weekend only to find out your school thinks you’re dead? That’s brilliant.
Now back to the main, most important, central theme of this whole experiment: will Issa and Lawrence get back together? I think so. Now, should they? Probably not. Issa has waaaaay too much going on (or not, lowkey) to be worried about trying to figure out how to play house with Lawrence, who has to grow the fuck up REAL QUICK and be part of the Lawrence x Condola ecosystem. I ain’t saying they need to stop speaking, but if she’s smart (she is) and makes good decisions (she doesn’t), this break up with Lawrence needs to be permanent-ish. What do you think?
Shanelle Genai: Molly is definitely self-minded but the way she could clearly see Issa needed to bounce back from that panel and hung out with her even though the awkwardness level was at kajillion, that said something. She also stepped in front of Issa to kind of block and shield her from the fake robber when he was pointing the gun at them. A selfish person wouldn’t do that, I don’t think. Also, shoutout to Cheyenne Thee Robber for being ratchet AF, limber AF and also selective AF for not taking Issa’s shoes. They say robbers can’t be choosers (or something like that), but clearly she was choosing taste.
Back to Issa and Lawrence though: HELL NO I don’t think they need to get back together—ever, actually. They have a lot of history, true enough, but I think relying on what you used to have to fuel what you could have next isn’t always smart. The reality of it is Lawrence is a father now and Issa seems to finally be getting in her groove. For her to try to finesse playing bonus mom and being there for herself and her friends is asking a lot. Issa no for me dawg, (you see what I did there?)
Panama Jackson: I do see what you did there. Also, Stanford is graduating low-level robbers and scammers? Cheyenne Thee Robber sticking folks for their papers?? What is the world coming to? And maybe you’re kinda right about Molly, but I need to see more. I don’t trust it at all. I’ll try to see it from that very positive perspective but it’s going to be hard for me. You know what I appreciated? I appreciated how Lawrence didn’t try to fight Issa about trying to make it work. It’s like he had a brief second where he was hurt but he also realized what he’s asking of her and that’s growth that I can appreciate. You know what I appreciate about this show? Just how honest they keep the relationships.
You watch it and it’s specific to them but works for most of us. I remember where my life was 10 years out from college and all of those insecurities were there; the feeling successful in one area but lost in others. They really nail the friend groups. And I have to admit, seeing Molly and Issa walk around and offer each other advice—I’m totally here for Issa telling Molly that she was never running behind Omari—was nice. I’m really excited to see what happens with everybody on this victory lap. I hope you’re not right that “ain’t shit changed” and Issa is still trying to figure it out by the end, but also, that would probably be the most true-to-life conclusion. Le sigh.
Shanelle Genai: I’ll have to also reluctantly co-sign and big up Lawrence for not fighting back, too. Though I am definitely anti-#LawrenceHive (woot, woot!), he didn’t push and I have to give him props for that. As far as the rest of this season goes, you know what they say: all’s well that ends well. Seeing as how Insecure has quite literally nailed every last season finale up until this point, I have no doubts that however the story goes for our fave friend group, it’ll be more of the same goodness.
Panama Jackson: You’re right. Whatever happens from here, I’m just glad we got five seasons of heat from the crew. I don’t know if any other show (I realize this is going be disputed almost immediately) has offered so much conversational fodder so specifically centered around young Black professional life. Literally every show has something that could break the internet. Also, I don’t know I’m part of the #LawrenceHive, but I am definitely Team Lawrence while also wanting the best for Issa. Until next week...
An all-new episode of Insecure premieres Sunday, Oct. 31 at 10 p.m. ET on HBO and HBOMax.
Straight From 
Sign up for our free daily newsletter.