Insecure gets ready to say goodbye in “Chillin’, Okay?!”

Every season of Insecure has an episode where our girls get together, get real, and show us how they’ve changed. From Coachella to “Malibu” to the search for Tiffany, these are usually some of the best episodes in the series. “Chillin’, Okay?!” has the difficult challenge of not only being as good as those episodes, it’s also the last time we’ll probably get to see these characters interact like this.

Penned by Fran Richter and directed by Amy Aniobi, two long-term Insecure insiders bring a near-perfect episode to life. Aniobi is also head writer and co-executive producer and has been working with Issa Rae since Awkward Black Girl; Richter started writing for the show in 2018 and has cameoed in episodes. The two have an intimate knowledge of the show and these characters that makes them a perfect choice to handle the task.

This season’s premiere gave us a destination moment, so it’s wonderful that “Chillin’, Okay?!” lets the girls have a night in at Issa’s. At this stage, all I want is to sit with these characters. It’s also a brilliant homage to Waiting To Exhale, one of the best movies about Black female friendship ever made. Like that film’s sleepover scene, Insecure’s is also filled with reveals and moments of joy. Their friendship also feels matured; they’re all able to speak freely. It’s difficult to imagine these characters having these conversations in earlier seasons when Molly would’ve cut anyone who questioned her.

Tiffany tells everyone she’s moving to Denver, which acts as a catalyst for everyone to stay in and make big decisions. Well, almost everyone. Molly decides to give Taurean the green light. Issa decides to stop being wishy-washy and stick with Nathan (mostly). Kelli… is there to be funny. Of course, Kelli is sad about Tiffany moving away (there’s a brief moment where Natasha Rothwell perfectly conveys the pain that Tiffany didn’t tell her first in a single line), but otherwise she’s just there to crack jokes about Daniel Kaluuya.

They do quickly introduce the idea that Kelli may want to change careers. She no longer wants to help rich white men get richer. This would be great if anyone watching the show knew Kelli had this problem before now. We know Kelli works in finance and we’ve seen her give Issa financial advice, but there’s never been a hint that her work was unfulfilling. Tiffany’s concerns about moving to Denver after her breakdown last season (“Lowkey Lost”) make sense. We’ve seen Tiffany grapple with this issue before, while Kelli just sort of goes where the story demands.

“Chillin’, Okay?!” is almost a bottle episode. We spend the majority of time with Issa, Molly, Tiffany and Kelli. Perhaps, “Chillin’, Okay?!” would’ve been perfect if it had just locked us in with the girls for the night. Instead, the episode takes brief detours to check in on Lawrence and Condola. Lawrence has moved back to Los Angeles. The two are doing great and love Elijah. Lawrence puts up shelves. Good for them. Isn’t that lovely. Sadly, I could not bring myself to care. We already knew Lawrence moved back, but was anyone really that invested in their co-parenting journey?

It’s great that Lawrence is finally being a good dad, but every time they cut to those two I just started wondering if Doritos are actually good in cookies and how many joints Kelli could smoke in a single session. It’s not that I wouldn’t have been happy with an update on Lawrence and Condola later in the season, but it just felt unnecessary here. It does draw an interesting parallel to where Lawrence is in life versus Issa, though: Lawrence has a kid, a great job, and a nice place. Issa is still partying with her girls at sleepovers and dealing with irritating tenants.

It’s not hard to imagine that Issa would rather be in a nice home with Lawrence. Her drunk dial makes sense. If the episode had been entirely focused on the girls, Lawrence’s call at the end would’ve felt like even more of an intrusion. After Nathan finally tells Issa he loves her, Lawrence’s presence should feel more startling, but like Molly, I don’t want Issa to be a stepmom. I want her to stay away from that Lawrence-Condola mess. At the same time, Issa didn’t even sound that excited when Nathan finally said what she wanted to hear! If you want Condola’s babydaddy, just figure it out, Issa!

Stray Observations

• I absolutely agree that Daniel is Issa’s hottest ex.
• Disappointed that Issa would offer soggy joints to anyone, but it’s in character for her! She’d want to look cool and roll her own joints, but also she wouldn’t be great at it.
• I still like Taurean and Molly! Molly’s crush is really cute. I like that they immediately started making fun of her for wanting to take a work call.
• Tiffany and Derek moving to Denver makes sense. There have always been theories about cheating between those two and I’m sure this will add fuel to that.
• Always happy when we get to see Black women smoke weed on TV.