‘Insecure’ Season 5 Episode 1 Recap: “Reunited, Okay?!”

Insecure owned my Sunday nights in 2020. Between protesting police brutality and the isolation of sheltering in place, we all gathered around the (Black) Twitter water cooler to debate, meme, and relate to these characters we’ve grown to love. Season 5 returns at a slightly less chaotic time in the world, and also apparently in the lives of Issa, Molly & the gang.

With dust settled from the season 4 finale’s bombshells — Condola’s unexpected pregnancy, Issa & Molly’s falling out, Tiff’s battles with postpartum depression — we find the crew headed back to where it all began: Stanford for their 10 year college reunion…. As the title states, we’re all “Reunited, okay?!”

From the opening shots — mountains? Winding roads? Uh oh, we’re not in LA anymore — Insecure season 5 is giving us the unexpected. Kelli carpools to the reunion from LA; meanwhile, Issa’s gliding off a flight to San Francisco… is she going to meet Lawrence? Did he take the job? Not sure… but for now, she’s headed to meet everyone for the reunion (including Molly).

The crew strolls around campus before a reunion party “looking like a diversity brochure,” with Issa pretending to remember people — including an alumnus who used to flirt with Derek by whispering Mystikal lyrics in his ear, mating call of Black millennials of a certain age.  This episode feels like a time capsule for viewers who’ve come to identify with the characters, the milestones in their lives, & cultural touchstones they mark them by. A love letter to the early aughts.

Insecure is at its funniest at the reunion party. As our characters arrive, we’re treated to a Black female flutist doing The Humpty Dance to “Blow the Whistle”. Now, Insecure gives me fomo from aerial b-roll, so I’m not shocked to want to enroll at this fictional version of Stanford because it seems Black as hell.

They run into a fellow student Cheyenne who I’ll call a walking red flag! Tiff, ever grown & wise, opts out because Chey was always “too crazy” for her, while Molly, Issa, Kelly & their old friend immediately lauch into hilarious lyrics from their former rap group Trap Habit: “Tricking niggas is a habit. // Leave ‘em with the baby. Tell his mama she can have it!”

“Ain’t shit changed” becomes Cheyenne’s refrain… and Cheyenne our cautionary tale: what would our characters be like if they’d never evolved?

Audience criticisms of Kelli’s lack of character depth were tackled head-on after a mix-up leads reunion organizers to believe she’s died. During an in memoriam tribute, all her academic peers had to say about her was “funny”, “great stanky leg,” & “always carried a purse.” If I had to tag myself in the season opener of Insecure, it’d be Kelli Prenny doing a melancholy stanky leg in a powder blue babydoll dress & white gogo boots to commemorate her own death.

My favorite scene from the Season 5 trailer was Issa in the mirror reconnecting with her younger self. And the episode more than delivers. No rapping this time, but one of my favorite Insecure staples is Issa hyping herself up in the mirror. And she’s got plenty reason to be proud & reflect this time around: she’s been flewed out by her alma mater to speak on an entrepreneurship panel.

Of the panelists, Issa’s at the earliest stages of her entrepreneurship journey & shown in sharp, awkward relief to them & their assured, press-ready responses. She can barely remember the name of her company & the panel host mispronounces it as The Blow-CC instead of The Blocc…. Even still, Issa’s cheering section bigs her up before they split for the afternoon — Kelli to band reunion — Tiff to an AKA thing with Derek — leaving Issa & Molly to chill…. With drinks…..

In a show like Insecure where there’s so much to love, the wardrobe and accessories stand out! Green plaid satin co-ords for Issa & Molly with the earth toned suit, mules, & Bottega clutch. Earlier, the Telfar bags with their Stanford sweatshirts. Molly’s Cartier watch! I’m vehemently anti-capitalist & I still yelled out “STUNT ON EM!” as Issa stole the pair a handful of drinks from the bar.

Over lunch, there are signs of hope for the show’s most important friendship. Prompted by a protest flyer being dropped on the table, Molly asks if they’re gonna be ok…. Issa wonders if she means the world or … them? Before we get the resolution we crave, Kelli hits the group text with plans for the gang at an Oakland club Issa was thrown out of in undergrad.

Back to the accessories, and not to victim-blame, but Issa & Molly are robbed at gunpoint on the way to Oakland at a liquor store detour made at Cheyenne’s suggestion in the funniest scene of the episode. Between gasps of a complete meltdown, Cheyenne observes that Molly’s watch is Cartier – almost immediately revealing she’d set up a stick up with the help of  a friend from the Bay – a masked assailant who accidentally drops her name. Cheyenne yells her refrain “Ain’t shit changed” while riding off into the night with her ill gotten drip.

Molly & Issa explode into laughter recounting their harrowing experience to Kelli & Tiff & it’s the most joyous interaction we’ve seen from these two since season 3 – though we saw glimpses during the block party before the fight to end all fights. Even though it took a near death experience, you love to see it.

At brunch the next day, the girls give Kelli a proper memorial & Issa & Molly agree to let go of expectations & just move forward.

Back in LA, Kelli ponders her mortality & asks podcast listeners what they’d do with a second chance at life. We hear this over Derek & Tiff with their baby Simone in the Stanford legacy onesie. With Molly in the mirror pondering herself & her hair – maybe foreshadowing the big chop we saw in the trailer. And with Lawrence still in LA, picking up Issa from the airport with a kiss.

After an awkward car ride, Lawrence’s open ended “should we…” meaning…. should we go upstairs into your place? begins the hardest scene to watch. I’ve come to expect the concrete questions in Insecure have abstract answers. Are we… Molly and Issa and the world… gonna be ok? Should we… Lawrence & Issa, continue this complicated relationship?

Like this season so far, this breakup feels mature and final. But if I’ve learned anything the last 4 seasons, it’s to expect the unexpected from Insecure.

Additional Thoughts:

• If Molly & Issa are at “ma’am status” with Gen Z folks, then so am I.
• Omari trying to “reapply for the fuckbuddy scholarship” gave us yet another beautiful Black man to argue about on Twitter. Thank you, Issa… though I don’t think we’ll be seeing much more of him or his king size bed.
• Everybody needs to listen to Kelly! Molly asked for advice on how Kelli patched her relationship with Tiff & it at first seems like gibberish but the jist was: time, effort, be there for her, laugh at jokes, and fill her immediate needs where you can. Molly succeeds at breaking the ice later by asking if a grumpy Issa has eaten. Later Lawrence pretends to laugh at a joke Issa makes in the car as an effort to preserve their relationship… Kelly was on to something!
• And Kelli’s “what makes her hair grow?” advice sounds silly but the groupchat right now is heavily about OUR hair growth remedies (jamaican black castor oil, henna, amla, & coconut oil btw)…
• They didn’t have to do Issa’s shoes like that!!

Rebecca O’Neal is a stand up comedian and writer in Brooklyn. She hosts a comedy show – Angel Baby at Purgatory – in Bushwick (November 4th & 27th). Check out her jokes on Comedy Central.

Watch Insecure Season 5 Episode 1 on HBO Max