‘Insecure’ Season 5 Episode 8 Recap: “Choices, Okay?!”

There’s nothing like a big decision to make you question… well, everything. And in episode 8 of the final season of Insecure, Issa’s grappling with TWO very big “choices, okay?!”.

Her love life is as stable as we’ve ever seen it and her career potential seems limitless after securing a big figure offer from NBW. But when faced with the option of moving in with Nathan – and an unexpected chance to reconcile & partner with Crenshawn, stability might seem a little safe as we see Issa hilariously pondering what could be.

The fantasy sequences were again the highlights of this week’s episode. (And the show knows it: having Mirror Issa, a fantasy herself, reminisce about dream-yeeting Condola’s baby into the trash!) But considering how much Insecure has played with the passage of time this season, I wasn’t sure Issa’s corporate-track fantasy was a fantasy at all… until Ty Dolla $ign showed up to burst Issa’s immaculately dressed bubble in first class, name dropping Crenshawn as “something like a hood hero or something.” After her U of M panel (hosted by Elaine Welteroth!) during which Issa admits success has her out of sync with LA, that news hits different. Nightmare scenario.

Even Mirror Issa has a hard time buying this version of events. “I could get with that?” The styling is slick. The West Hollywood property is lush. Nathan & Issa look like a couple from a ’90s Black Rom Com – which is where Fantasy Issa stops suspending her disbelief. Issa’s team at The Blocc ran like a well-oiled machine, spoke like a Greek chorus, and dressed like dramaturgs. Maybe it was the straight hair, maybe it was the fear of selling out but it’s clear Issa wants to do more with a vision of her future than possibly “get with” it. As she should!

A visit to Crenshawn’s shop presents a vision of an alternate path. Issa’s a hometown hero! She’s learned to play spades! Her natural hairstyles are more elaborate than ever! Inglewood Mayor Tyra Banks presents her the key to the city! But just as in the other fantasy, doubts manifest themselves in the form of Ty Dolla $ign, this time in a “This water hits different” NBW ad on the side of a bus. We then see her fantasy life with Nathan looks a lot like her current life with Nathan. She’s the hood hero this time but still plunging hair out of tenant’s toilets at the building where she’s still the super. And before she even gets to plunge, Lawrence pops up in her fantasy, because of course he does, at which point it becomes a CLEAR nightmare.

At Molly’s parents’ house, Kelly is helping the Carters with their estate in the way only she can: with humor, empathy, and grace. Met with their parents’ obvious discomfort at the task at hand, Molly plays the task master while her youngest brother finds busy work & flees. With a lot of patience, they make it through the overwhelming task with a will!

Taurean continues to be a huge green flag after again being a wonderfully empathetic human to Molly at her most vulnerable. When she understandably cancels their date after the draining day she’s had with her parents, he doesn’t make it about himself or try to Frankenstein together a new plan. He lets her know he’s there for her & sends wine & wings. I’m rooting for these crazy kids… and I say “kids” in that this is a very emotionally-intelligent adult courtship.

Issa spends a lot of time in her head this week & just when we think we’re getting a nice, grounded dinner scene with Nathan in the real world narrative present, Lawrence’s voice pops up hoping she’s happy. Mr. Not Now himself! But this time, Issa’s not in a fantasy. She’s in her home. With her boyfriend. Who she loves – and may move in with. This isn’t Mirror Issa. It’s Issa-Issa, I fear. And I think that’s her fear too.

The nearing of the end always elicits thoughts of the past, and with only two episodes left in the series, it makes sense for Insecure & its characters to be getting this existential. And now one asked but my fantasy for Insecure: if I can’t get another season, maybe a UK-style Christmas special?

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Additional thoughts:

• Quoia does not play about Issa! Even in the face of Crenshawn’s “sexy ass apology.” I hope she gets a nice size chunk of that NBW payout – if only to move out of her parents’ place.
• The transitions out of the fantasy sequences where Issa breaks the fourth wall were so funny. The editing in this episode overall was so effective!
• I love that they’re giving Kelly’s story a little more meat but I’d love to see Natasha Rothwell play a character whose main function isn’t solely helping other people… even though she swears off helping rich white people this time. No White Lotus.

Rebecca O’Neal is a stand up comedian and writer in Brooklyn. Check out her jokes onComedy Central.

Watch Insecure Season 5 Episode 8 on HBO Max