‘Insecure’ Season 5 Episode 7 Recap: “Chillin’, Okay?!”

In a final season that’s played with tone, pacing, & genre as much as this one has, Insecure still manages to make the familiar feel fresh in this week’s bottle episode: “Chillin’, Okay?!” (Season 5, Episode 7) — buoyed by affectionate visual nods to A Different World & Waiting to Exhale, and handled deftly under the direction of the show’s head writer Ami Aniobi. With three episodes of the series remaining, keeping our characters in one place sacrifices a lot of the messy plot points we’ve come to love – but more than makes up for it in character development for not only Issa & the gang, but co-parents Lawrence & Condola as well.

It’s most likely one of the last times we’ll see the squad together, so the intimate setting feels more than appropriate. Molly, Kelli, and Tiffany meet at Issa’s for a much needed (and long overdue) girls night that gets thwarted by spa mishaps & spontaneous confessions. The audience has preguntas & this week – thanks to “Questions in a Hat” (an amazing narrative device and game I definitely want to play with my friends if only for all the synchronicity it brings), we and our characters get some answers.

Though Issa – after putting on some Keyshia Cole & Diddy – suggests the game, she enjoys it the least, dodging questions & making up more rules than Black people playing uno. The question asker doesn’t have to answer the question? Ok, Jan. But our quartet is at a mature point in their friendship, past giving superficial answers and easy outs – or enabling each other’s harmful patterns. In “Chilling, Okay?!” we see our main characters at their best – and most open and vulnerable.

It was a tight contest, but Molly is the friendship MVP in this episode. She notices when Issa is uncomfortable talking about Lawrence, spiralling & jumping to conclusions about how he & Condola “got back together” & suggests the group get dressed for dinner. She’s the first one to break the loaded silence after Tiffany’s bombshell confession about moving to Denver, like the omelet, with Derek. And most importantly, she stops Issa from making an ill-advised call to Lawrence in the middle of the night. Crossfaded. Issa was double fisting clear liquor mere hours before… not on Molly’s watch.

Her friends’ bullying (re: being inconsistent) worked. Once their night concludes & Issa finally has her “I love you” to Nathan reciprocated, Lawrence — the king of bad timing — calls & is sent to voicemail. The final shot of the episode shows Lawrence as a man with his life together, and his mind made up, who knows what he wants. His kitchen was cleaner than any single man’s I’ve ever seen.

Meanwhile, Issa, surrounded by chocolate chip & Cool Ranch Doritos cookie crumbs, seems less than enthusiastic about her current relationship & my mind goes back to her only straight answer during Questions in a Hat. To “what do you wish you could do over?” she answers “I just figured out what I’d wanted to do sooner.” Does she mean professionally? Does she mean personally? All of the above?

Molly’s words to Tiffany are the theme of the episode: “You gotta be really intentional with the people you love.” Nathan opens up about his avoidant attachment style and agrees to work things out with Issa. And I was genuinely proud of Lawrence & Condola’s co-parenting progress after their brutal dynamic earlier in the season. For all their growth though, it was clear Lawrence’s heart & mind were elsewhere while thinking about what happiness would look like for him.

I’ve oscillated on this but with the season finale looming, I want Issa & Lawrence back together. If Issa can get out of her own way, I think it can happen. I want the new emotionally-intelligent Molly to give things with Taurean a real shot. I want her to block Dro!!! I’m not sure if I’ll get what I want (and I’m sure this final stretch will give the timeline plenty to argue about) but Insecure always gives its fans what they need – including all designers featured in this episode being Black women, from accessories to clothes to shoes! I’m gonna miss this show so much.

ADDITIONAL THOUGHTS:

• Kelli had too many funny lines to count (“A bitch got preguntas!”) but I’m most grateful to learn that “Cali sober” still gives her the latitude to be a stoner who smokes soggy joints.
• “Is he Love or is he Jones?” – Molly has never seen Love Jones! Issa can’t play spades! These two are perfect for one another.
• “Which of your friend’s exes would you fuck” is such a chaotic question… but I’m glad everyone agrees it’s Daniel. Pure fan service.
• “These my going out titties but they can stay home.”
• Not Issa saying “Oh Ok” to Nathan’s “I love you”. Is she Han Solo???
• Amanda Seales is consistently given heavy material & handles it beautifully! The woman can emote.

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

Watch Insecure Season 5 Episode 7 on HBO Max