Reunited, Okay?! – Insecure Season 5, Episode 1 Recap

Photo Credit: Glen Wilson

This post is in partnership with HBO. As always, thoughts and opinions are my own.

The fifth and final season of Insecure is here, and I could not be more excited to watch this journey wind down.

Let’s jump into it. 

Reunion – The crew goes to San Francisco for their 10th year Stanford graduation reunion. Aawww. Our babies are all growed up and in their 30s now. Kelli road trips there with Tiffany and Derek. On the way there, they talk about how Molly has been sub-gramming her recent breakup. Aawww, sis is in her feelings.

Issa gets on campus, and to make things awkward, her and Molly are wearing the same sweatshirt. Any who, Issa tells em’ she got flewed in, because she’s on a panel on entrepreneurship to talk about her company, The Blocc, which is an acronym she can barely remember.

Photo Credit: Raymond Liu

Memories – But wait, Kelli had to get a name card manually printed. Why? Because according to the reunion book, she died. There’s a pic of her under “In Memoriam.” Why’d they kill my girl? She finds humor in everything so she figures it might be a chance for her to try on new identities. One of them is not gon’ be therapist because when Molly asks Kelli for advice on what to do about the distance between her and Issa, all she gets is “you need time.” Dr. Rhonda ain’t gotta worry about her job being taken. 

That night, at the welcome party, they run into Cheyenne, who used to be the third person in their, clearly failed, rap group “Trap Habit.” She’s still in these streets and is killing it as a dancer for Saweetie. Molly catches up with Derek, and 2 other dudes. One of whom is named Omari and is newly divorced. The other two make themselves scarce, because Omari and Molly had a friend with benefits situation in college. Could this be a chance for a re-ignition? We’ll see. 

The “In Memoriam” tributes come up and Kelli’s face pops up. One of the memories people attribute to her is her spectacular stanky leg, which the DJ then plays to honor her. She whines “I’m so much more than this,” as she sees her picture on the screen and does her stanky leg. 

Back in her room, college Issa with braces drops in on her in the mirror to get life updates. How’s life been for the last 10 years? Do they have a man? Well, it’s complicated. Did she become a lawyer? Nah she never wanted to be that anyway. Is she still besties with Molly? I mean, they cool. 

Issa says she owns a company called “The Blocc” and shows throwback Issa what she’s wearing. College Issa is lowkey disappointed by their life. Before she goes, now Issa tells old Issa to start a photo sharing app called ISSA-gram. “What’s an app?”

The Joke – Later that night, they pile into Tiffany’s car with Cheyenne, who has invited them to go to an old reggae club that Issa apparently got kicked out of at some point in college. In the car, as the others are having a good time, Kelli is somber because seeing herself “In Memoriam” has her reflecting on the legacy she’s leaving. She snaps on the girls, who aren’t taking her serious, wondering if she’s just a joke to people. 

Cheyenne suggests they stop at a liquor store, like old times, buying their own drinks and sneaking it into the club. As Issa, Molly and Cheyenne exit the store, a man pulls out a gun and tells them to hand over their bags and jewelry. Turns out, Cheyenne set it up, and walks off with ol’ dude and their stuff (including Molly’s Cartier watch. OUCH). Besides their clothes, the only thing she doesn’t take are Issa’s shoes. YAY and SHADE? Issa: “I forgot I hated her.” 

When they get in the car and tell Kelli and Tiffany what just happened, they fall out laughing. They’re laughing, without the tension they’ve had, and bridging the invisible gap. It’s cute. But also: I’d still be pissed to be robbed. Cheyenne ain’t shit. 

The next day, as they’re eating breakfast, the girls give Kelli a eulogy, talking about how important she is to them. She needed to know she’s more than just jokes to people and it’s sweet, and creepy, at once. Sweepy, if you will. 

A classmate walks up saying they missed the party the night before. Yeah, what had happened was… Oh, and he gives the message that Omari was looking for Molly.

Photo Credit: Raymond Liu

Move Forward – After breakfast, Molly and Issa walk out together. When asked about Omari, Issa says she loved the fact that when they were in school, Molly wasn’t pressed for attention and certainly not for these men. But that’s because in your early 20s, you feel little pressure to be a grown up. But why do they need to be burdened with time now? Issa says she just wants to move forward, and Molly agrees. 

Kelli gets back to her podcast, Prenty’s Preguntas. She’s reflecting on legacy. What would people change if they knew their time was about to run out and the end was near? How do people want to be remembered?

Tiffany and Derek get back home to their baby girl, Simone. For them, family is the key in that moment.

Molly is home by herself, looking at this version of herself in the mirror.

Issa lands back in L.A. and kisses Lawrence, who picks her up from the airport. When they get to her place and he steps out the car, she stops and says she’s had a chance to think. In that pregnant pause, he knows what she means (cuz he has a pregnant ex). All he can say is “Yeah.” She grabs her luggage… and goes into her apartment.

Season 5 of Insecure is “Onward, Okay?!” and the foursome is growing up, figuring out what’s important, and well, moving forward. It’s clear they are all in places of transition, and introspection. 

Issa and Molly’s friendship fractured last season, so seeing them heal the chasm is needed. People don’t talk enough about the heartbreak of sisterhoods ending, and these two have been by each other’s sides through thick and thin. I know we were rooting for them to find their way back.   

The DuBois are stronger than ever, and their love and stability as a unit stands in contrast to the perpetual singleness of Molly and Kelli (and Issa). I love to see it. 

And Kelli, who is constantly making us laugh. What we see now is her wish to be seen with more depth, because she is beyond the funny girl. It took her seeing what people would say about her in death, to reflect on the type of legacy she’d like to leave. I love Kelli, because she is a FREE Black Girl and oftentimes, people don’t know how to deal with her. 

I’m looking forward to the GROWTH we’ll be seeing this season. 

Insecure, it’s good to have you back.