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

As much as it pains me to quote Chad’s advice (quoting Mike Tyson) from the Lawrence episode, it feels appropriate for this week’s episode of Insecure: “Everybody got a plan until they get punched, my guy,” because our characters are truly “Struggling, Okay?!”… and at the worst possible times.

There’s been a lot of speculation about the fate of Molly’s parents after her insistence they plan their estates earlier in the season. Before that comes to bear, we get to see Molly at her most empowered (“Say my name! Now spell it!”) and most present as the episode opens with one of Insecure‘s signature sex scenes. Even though the actor’s face is obscured by … well, Molly… for his entire appearance, Insecure doesn’t pass on the opportunity to cast another hottie for the timeline to debate. Of course, narratively, this is where things have to come crashing down.

One thing Insecure does an amazing job of in this episode (and in general) is couching the heavy stuff in jokes. We learn Molly’s mother is in the hospital with what turns out to be her second stroke between Molly’s O-Face & a case of mistaken identity during which we’re initially led to believe Molly’s mom is near death & meet a bizarro version of the Carters. The doctor’s nonchalance at this mixup feels to me like a nod to the unequal treatment Black women face in the medical field & I wouldn’t be surprised if Insecure shone a humorous light on this issue.

Meanwhile, all the goodwill Issa and Nathan built up in their romcom episode is fading… quickly. These two make me nervous. Though the circumstances lent themselves to emotional vulnerability, as a viewer, I got whiplash from the quantum leap between “we said we should take it slow” in their first scene together, to “that’s why I love you” by the episode’s end. It was about 20 minutes for me and couldn’t have been more than 10 hours for our characters. Even before her run-in with Lawrence left her literally waffling in the hospital hallway, I wasn’t convinced about the lightspeed progress of their relationship. 

As someone who’s been with these characters for five seasons now, I can’t help but notice Issa’s dynamic with Nathan is just….weird! Before learning about Molly’s mom, the couple makes excuses to spontaneously spend the day together –  moments after agreeing to pace their relationship. On a way-too-relatable FaceTime with Issa’s mom, Nathan decides he’s her boyfriend to her visible delight. And later she drops an unreciprocated L-bomb on him because of how “patient” he is with her. 

Issa’s never struggled taking charge in relationships post-Lawrence… until Nathan. She’s weirdly flattered at him driving her around – even though I feel like he’d do as much for her even if they were still platonic friends. She’s celebrating the small things when he brings her coffee in bed – and it’s cute but it doesn’t seem like the Issa I usually root for. She’s never even this nice in the face of Molly’s kindness or thoughtfulness so I’m not sure why she’s so moved by Nathan being a good guy.

And for all of Molly’s growth, she’s clearly still taking on more than she can handle – insisting on maintaining all of her professional responsibilities, taking on her mother’s power of attorney, and seeing to her family’s needs while her mom is hospitalized. Issa shows up right on time to see to Molly’s – mirroring Kelly’s advice from the season opener about how she patched things up with Tiff. “What do you need? Are you tired? Are you hungry?”

Issa realizes both ladies are still dressed for last night’s hookups & offers to switch clothes in the bathroom so Molly will be dressed more appropriately for the hospital. Nathan being the good boyfriend-elect drops Issa off at the hospital, picks her up, shuttles her to Molly’s for a change of clothes, and reminds her not to starve Molly’s dog Flava Flav – who the pair almost immediately, but briefly, lose. 

The timelines inevitably merge by the episode’s end! And Kerry Washington’s direction of the running-into-your-ex scene really kicked me in the throat. The zoom-in on the baby. The pan to Condola. Lawrence popping up like a meerkat from behind the stroller. And Jay Ellis doing some of his best non-speaking work of the season with the resigned-Dad-face & damn-near-pallor at seeing Issa. I shouted “WHEW” outloud to myself seconds before the show’s psychic soundtrack echoed me… literally. 

My mind goes back to Nathan even after Issa’s run-in with Lawrence. His face wanted to say “you get it from your mama” while Issa described her mother’s post-divorce flakiness. With Issa’s criticism almost exactly mirroring Nathan’s sleepover recap to his coworkers (“She’s all over the place”) – and between the Steph Curry jokes and the fair weather commitment style… Nathan clearly observes that the apple doesn’t fall far from the Dee tree.

Our last scene with Issa & Molly treats us to more of season 5 Issa’s wise & pithy advice. Understandably, the stress of her mom’s hospitalization brings the otherwise recently very secure Molly’s doubts to top of mind. Issa is quick to remind Molly what an amazing person she is & how well she’s doing in life (“Bitch! Do YOU know YOU?” is the pep talk every friend wants to hear) before splitting to grab them coffee (& run into her would be Step-Baby!).

“Surviving, Okay?!” was a great peak into what growth for our characters looks like with variables thrown in. Yes, Molly has adopted a more balanced approach to dating, but a sick parent reignited her need to be in control of everything. She’d been living in the present & focusing on herself but the stress of the episode handily lent itself to leaning into old habits & anxieties. And for all her awkwardness & insecurity, our typically romantically assured Issa is showing us a giddy schoolgirl side of herself that… I unfortunately find unconvincing. Nathan seems to have his doubts & remains wisely tentative, too.

I’m not sure what the future holds for these two but after her reaction to seeing her ex, Issa’s declaration is starting to feel like I love you, but I’m not in love with you. The struggle!

Additional Thoughts:

• Issa not being a dog or pet person makes so much sense. Based on her indifference to Flava Flav &&& her awkward dynamic with pretty much every student she worked with at We Got Y’all, I can’t wait to see her potentially interact with Condola, Lawrence, and most of all lil Jah in the next episode. No way it’s not as awkward as possible.
• I’m looking forward to the weekly supplemental reading material this season – Turned Away at the Gate…. Because once they get to the gate, it really picks up!
• I need a The Blocc is Hot crewneck in that exact colorway, thanks.
• Aunt Kiki reminds me of about 5 of my family members. She was written maybe too accurately – from “Lord! Why are you trying to call her home?” to “Betty wanna pray on speaker!” – I know this woman.
• I’m enjoying how they’re teasing out more info about Nathan’s past. All of the characters are navigating parental relationships in this episode, but Nathan’s dad is a great foil to Issa & Molly’s frustrating but supportive parents.

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 on Comedy Central.

Watch Insecure Season 5 Episode 5 on HBO Max