Insecure Intermissions: Let’s Talk about Issa’s ‘Choices, Okay?!’

Every Monday, Very Smart Brothas Senior Editor Panama Jackson and Contributing Freelance Writer Shanelle Genai break down the latest episode of season 5 of HBO’s cultural flashpoint show, Insecure. Okay?! Spoilers ahead.

Panama Jackson: It’s that time of the week again—Monday—where we do that thing we do where we talk about that thing we all watched last night, Insecure. And this one is bittersweet for me because as it goes, this is my last (and second to last) byline here at TheRoot. My guitar gently weeps. Much like we witnessed in this episode, everybody has choices, be smart with them. With that said, I enjoyed this episode; Issa comes to face-to-face with a crossroads in her life, she finally made good with TheBlocc and they tryin’ put stacks-on-stacks on the table. But also, Crenshawn, an artist Issa thought she could change “the game” with has seen the error of his ways and is asking to get back into cahoots with her. We get treated to what could happen on either side of the equation, both with the pros and cons. Issa don’t know what to do, but like Molly said, what if there’s no wrong answer?

And poor Molly is goin’ through it trying to work on this estate stuff with her parents which actually made me feel bad for her because who wants to do that thing that we probably all need to do. Whew chile. Before we get into what we think Issa should do (and Molly’s new boo—the bars weak but the bank account bussin!), what did you think of the episode overall?

Shanelle Genai: First let me start off by saying how sad I am that this is your last recap! I promise to save all the sappiness for later but just know I’m feeling all the feels as I type this. Anywhooo, back to Insecure. Overall, I think this episode did a good job at preparing our expectations for where things might go by the finale. It’s clear, like you said earlier, that Issa has some choices to make. And although those flashes forward are often the most idealized versions in our head, I still think they helped paint a picture as to how life will shape up for Issa “Issa-Wood, Keys to the Muhfuggin City” Dee.

As far as her relationship (??) is concerned, what’s also abundantly clear is that she needs to make a choice between her head and heart: i.e. Nathan and Lawrence because it’s clear she’s still battling. Also, shoutout to Taurean for the wings & wine DoorDash. That was classy AF (read: charming and swoon-worthy) and now I’mma add “must door dash me wings and wine when I’m feeling low without me having to ask for it” to my list of future husband characteristics.

Panama Jackson: Yeah, I agree about it finally shedding a little light on what could come of the finale. I’m actually back invested in that. What a difference a day makes, ya know? And you know, I’m here for Taurean and Molly sitting in a tree. It’s cute because for most of this show I’ve not cared much for Molly and this season I actually kind of...like her. As I watched her go through it with her parents I wanted to give her a hug. I’ve never wanted to give Molly a hug before. Look at that growth, okay?!Also, you right right; Issa still has Lawrence on the brain and it looks like she’s about to dive in head first with NATHANIEL even though she’s not 100 percent in and I think we all know that leads to disaster. Or will. But maybe not. I don’t know but I hope not. Lawrence is still living rent-free in her brain, she gon’ need to handle that one way or the other. Choices.

Relationship(s) aside, and assuming both time-jumps were idealized versions of her future, were you compelled to pull for any one outcome over the other? National fame and recognition or “Keys to the City, Issa-Wood”?

Shanelle Genai: You know? As Keke Palmer once quipped: I hate to say it, I hope I don’t sound ridiculous but—is it bad I want both for her? Like, I think that’s often been a thing that plagues young, successful Black folks who want to give back to the city that shaped them but also reach a certain level of acclaim beyond it. It’s always, “be true to where you’re from and stay here “or “be a sell-out and grow beyond here” and I think that’s a hella unfortunate box to be put in. It’s almost as if you’re forced to choose between comfort and familiarity or expansion and greater influence and I think that Issa (and Black people as a whole) should be able to do both and not get judged for however way their fortune cookie crumbles.

Panama Jackson: I actually agree with you. I also don’t understand why she can’t do both. I don’t understand why it has to be an either/or proposition. Why can’t she build up The Blocc and partner with Crenshawn (among others) to do it? It seems like the company is either acquiring her company or paying to partner with her in some capacity? I need to see the terms here. But I didn’t see her deal (and let’s be real she didn’t either, she just looked at the financial offer) so perhaps it requires her to only work in-house? And one thing I’ve learned on this VSB journey, and especially with somebody like Damon is that he was able to level up nationally (and internationally, true story) while also being one of Pittsburgh’s favorite sons. Seems plausible. Hopefully she figures out how to do both; that’s the win-win for everybody. I do think it’s cute that Nathan’s part of both visions, though interestingly Lawrence was only there if she stayed local. Did you notice that?

Shanelle Genai: GANG GANG, long live VSB man. And oooh, I didn’t clock that but that is interesting! Which again, arguably speaks to that familiarity aspect I mentioned. Like, is she really choosing Lawrence because he’s who she loves? Or is she choosing him because that’s who she’s most familiar and comfortable with? And sure, being with someone for that long and then seeing them have a baby with a person who isn’t you right when y’all were working things out is probably triggering AF and makes you want that old thing back. But to your point, her only seeing Lawrence if she stays local is almost, ALMOST feels like she would’ve been settling. And to quote Caresha “Yung Miami” Brownlee: Ion like that.

Panama Jackson: Word, aight, any thoughts on Molly and her family situation to wrap this thang up?

Shanelle Genai: As far as Molly is concerned, I think we might get hit with like an unexpected death by the end of it. Like the estate planning, the heart attack, everybody coming together. It’s giving heart-breaking end coming soon and if that is the case, I’m probably going to be crying at the club with Molly into the next year. She’s always been strong and it feels like this season, she’s been coming together and falling apart when it comes to her family dynamic. I hope I’m wrong AF, though, but in the even that I’m not— I’mma stock up on tissues now. Plus, we only have two more episodes and I know it’s gonna be hella, lowkey, emotional AF, okay?!

New episodes of Insecure premiere every Sunday at 10 p.m. ET on HBO and HBOMax.