‘Insecure’ Season 5 Episode 6 Recap: “Tired, Okay?!”

Issa’s opening words to Condola beg the question of Insecure Season 5 Episode 6. “Can we just pretend like this isn’t weird?”  Please! Can we? Because “Tired, Okay?!?” turns the cringe-factor between Issa & Nathan, Issa & Crenshawn, and Nathan & … everybody up to 11. And though our girl Molly has some hilariously cringe-worthy moments herself, she’s extended equally impactful moments of warmth & grace by, of all people, her snarky coworker Taurean – moments Issa & Nathan’s storylines are sorely missing. 

We’ve rarely picked up where we left off this season, so I shouldn’t have been surprised when what I initially believed was Issa’s most mature moment this season gave way to what turned out to be the season’s funniest moment by far (under Natasha Rothwell’s direction!). Issa was a little in her head about a potential romance between Nathan & Resha last week & now she’s having full-out fantasies about meme-yeeting lil Jah into hospital linens, Sparta kicking Condola into the trash, & pump-fake checking Lawrence with more comical threats of violence to the tune of Flo Milli’s “Like That Bitch.” Reality seems to be getting in the way of all of our characters’ intentions & choices this week. 

Post hospital-fantasy, a scan of Lawrence’s instagram reveals he’s moved back to town & Issa’s day gets worse from there. Insecure is great at funny sex scenes, but as our main character tries to goad Nathan into returning her hasty “I love you”, hot or not, it was a nightmare to watch. GIRL WHAT ARE YOU DOING? She’s later professionally shot down by some unfriendly Black Gen Z art hotties she hopes to book for The Blocc’s Art Walk, but Crenshawn’s bad press has gotten to them first. Quoia unflinching loyalty in these scenes provides some much needed relief. 

Issa’s attempted peace-talk Crenshawn goes about as well as expected. He hits her with some hard truths she’d tried to write off as “miscommunications” & drops the theme of the episode: “You made them choices, so own ‘em.” He also pulls out a mock up of his new crewneck drop inspired by their interactions. It bears the word “Integrity” in art deco Great Gatsby font on an ombre tie dye background. I think it’s a wack design but I agree it’s a gut punch, especially with the day Issa’s been having. 

The second funniest moment of the season comes in another of Issa’s Scrubs-like fantasies… but this one is more of a nightmare. Issa doubles over, gasps, and all but starts shaking, crying, & throwing up seeing imaginary-Condola at the same food truck at the same time. And fake! Condola doesn’t hold back hilariously confirming Issa’s worst fears: Condola’s got the version of Lawrence she always wanted. He makes a billion dollars a month! He moved back for me! We’re engaged! His dick is bigger now! Condola then answers Issa’s 300 kick from the earlier fantasy with a roundhouse into a nice big pile of LA trash. Honestly, I cackled mainly because we’ve never gotten to see Christina Elmore be this damn funny!

Nathan has plenty of reasons to be “Tired” this week too. Between Issa trying to manipulate a confession of love out of him during frantic sex and getting no support from The Clips’s owner in the face of his coworker Suge’s entitlement & lack of professionalism, Nathan ponders leaving LA. 

It’s not hard to see Suge’s behavior as an extreme foil for Issa & Nathan themselves – what happens when people truly skirt the consequences of their choices? Though I get why he did it, Nathan broke barbershop code & took one of Suge’s long-suffering clients (“I’ve been here so long, my girlfriend’ll think I’m cheating!”) and said he could “take the heat”, but his coworker was more upset than expected & resorted to some extremely low blows about Nathan’s mental health. And Suge’s “Justify it however you want. That shit was foul.” could have been taken right out of Crenshawn’s mouth. Insecure always does a great job of creating parallel conflict dynamics where the solutions are not clear & there’s plenty to debate. Can’t wait to see what the timeline says about this one. 

Neither Issa nor Nathan seemed to have learned much from their individual struggles & come together at the episode’s end for more clunky and opaque communication & awkwardness. Issa resorts to small talk instead of opening up about running into Lawrence before pivoting to the elephant in the room: Why hasn’t Nathan said I love you back? He handles this in what I’d consider the worst way possible. Gets defensive. Blows her feelings off. And she blows his off too. He begins to share what’s taken place at work when she hijacks it to see her affections returned.

It’s a mess. No one wants to hear “Are you serious?” and “This is dumb” when they’re pouring their heart out… unfortunately this is exactly what Nathan says to Issa. And instead of Issa even superficially investigating th frustrations of her boyfriend who she claims to love, they tomato/tomahto the situation, call the whole argument off, & end the episode drinking wine in silence on opposite ends of the couch. 

Listen! I’m tired too! I want Issa & Nathan to make the obvious choice & breakup. I want Molly to be easier on herself. I shockingly want her to possibly pursue something with Taurean??? I want Nathan to give other people the same latitude to express their feelings he expects to be given with the expression of his. I want Issa to never contact Crenshawn ever again lol. And I want her to stop thinking the grass would be greener with Lawrence because as we saw a few episodes ago, she clearly dodged a bullet – and no amount of doomsday thinking or catastrophizing or Frankensteining what he & Condola’s life must be like from a hallway glimpse & a few IG posts is gonna change that. 

The only true viewer satisfaction I got this episode was Molly’s mom being stable & awake. Thank you God, thank you God, Thank you God. Beyond that, the character’s fates are all left up in the air and I’m very curious to see where they land.

Additional Thoughts:

• “FUCK LAVENDER!”
• Kendrick Sampson is a great dramatic actor! Every time someone is coming at Nathan’s mental health, I truly believe Sampson’s reactions. I also truly believe Nathan’s complete lack of compatibility with Issa is driving me nuts. All of their conversations are like “Who’s on First?”
• I really ship Molly & Taurean? He’s got good taste in whiskey & beyond the wisecracking facade, he’s an empathetic person who’s cute af when he’s crushing (“My mom had a mug… *hearteyes*”).
• Resha cracks me up & gets the best lines: “When I get tight, my braids too do!” And doing fulani braids with ballerina-length acrylics is no easy feat so we’re gonna let Resha slide this time. 

Rebecca O’Neal is a stand up comedian and writer in Brooklyn. She hosts a comedy show – Angel Baby at Purgatory – in Bushwick (November 27th). Check out her jokes onComedy Central.

Watch Insecure Season 5 Episode 6 on HBO Max