When we last saw the guys and gals of Insecure at the end of its fourth season, they were all at inflection points in their lives. Tiffany (Amanda Seales) and Derek (Wade Allain-Marcus) were dealing with her increasingly severe postpartum depression, Molly (Yvonne Orji) and Andrew (Alexander Hodge) broke up, and Lawrence (Jay Ellis) got a new job in San Francisco, then found out that his ex-girlfriend Condola (Christina Elmore) was pregnant, interrupting his budding reunion with Issa (Issa Rae).
Prompted by all these changes, Issa and Molly finally called a truce in their escalating fallout and met up at their favorite Ethiopian restaurant to try to find their way back to each other. Now, as the fifth and final season begins, everyone involved is trying as hard as they can to reevaluate how they ended up where they are — which, in a lot of ways, is right back where they started.
Picking up two months after the finale, Issa, Molly, Kelli (Natasha Rothwell), Tiffany, and Derek are headed to Stanford for their ten-year college reunion. The temperature between Issa and Molly is still cool, but it’s clear they’ve both agreed to try to mend their relationship. Issa has been invited to speak on an alumni panel for her organization the BLOCC (Black Life Opportunities Culture and Connection), which boosts her ego and self-confidence. Molly reveals that she’s back in therapy with Dr. Rhonda — a revelation that made me physically clap my hands in joy. And as usual, Kelli finds herself in the middle of shenanigans. Stanford thinks she’s dead for some unknown reason and has printed an In Memoriam in the alumni magazine to that effect. (“Maybe this is a good time to get off the grid. I do have some other identities I’ve been meaning to try out.”)
Later, Molly pulls Kelli aside to ask her how she dealt with the fallout between her and Tiffany during her pregnancy. Wisely, Kelli advises Molly not to force a closeness with Issa that isn’t there yet and to keep showing up as her friend. It’s a nice, funny moment that reminds us that the women in this group do have relationships with each other outside of their designated “best friend” pairings.
At a mixer later in the day, the girls run into an old friend Cheyenne (Taja V. Simpson), a member of their college rap group who “left early to go dance on tour with Ciara.” She greets them warmly and perhaps a bit too enthusiastically. But aside from Tiffany, who deems her “too crazy,” they’re all happy to see her and relive their college days. Cheyenne’s energy is … a lot, and she admits to sneaking into the event so that she wouldn’t have to pay. But what better time to get a little crazy than at a reunion?
Ever the wingman, Derek very casually shoves Molly into the waiting arms of an old hookup, Omari (he’s divorced now!), who still has a thing for her. They chat briefly about the original terms of their relationship, but two months out from Andrew and freshly back in therapy, there’s definitely the sense that Molly should maybe head in the opposite direction.
The event’s alumni memorial video rather hilariously only has superficial quotes commemorating Kelli’s life. (“She had the best Stanky Legg.” “She always carried a purse.”) But it’s clear by the look in her eyes that this upsets her. Kelli has often been relegated to the role of comic relief on the show because it’s where Natasha Rothwell shines. But it is good to see a more sensitive side of her, even if it is fleeting. Cheyenne leads her in a quick rendition of the Stanky Legg on the dance floor, and for a while, all is forgotten. (Always on brand, Tiffany daintily participates with a Champagne glass in one hand, a tiny purse in the other, and a little shimmy.)
Right before the panel, Issa runs into “Throwback Me” — Mirror Bitch, but younger. The younger Issa is excited to see her future self but is slowly disappointed, as the current Issa tells her with increasing trepidation that their life did not quite turn out the way they had planned.
But it’s at the panel itself (in a gorgeous green plaid suit) where Issa really starts to doubt herself. Aptly titled “Finding Your Path,” the other speakers are all articulate about the lessons they’ve learned along their business journeys. Issa, however, struggles to feel stable in the choices she’s made and realizes that she’s not sure if the BLOCC was the right one. It’s reminiscent of her time at We Got Y’all in season one, when it was clear that she didn’t have passion for her work. But now, the work she’s doubting is her own. She’s the one who has to come up with the answers.
Later, Issa and Molly steal drinks from another class’s mixer and chat while they walk through campus. Molly tells Issa about Omari’s interest and rattles on about her suspicions about the end of her marriage. Sensing Issa’s reluctance to engage, she quickly pivots to comforting Issa about her middling performance on the panel. As they continue to mosey through Stanford’s grounds, Issa remembers how she and Molly met and became friends in the first place: “I was like, ‘I want to be friends with this girl. She cusses so eloquently!’” The memory eases the tension between them enough for Issa to admit that she still feels inadequate in her work life. When they get lunch, Molly has her a moment of vulnerability and asks if they’ll be okay.
On the way to Reggae Gold later that night, the girls plus Cheyenne sing along to The-Dream in the car. Kelli is still upset that no one at college seems to remember her well, lamenting that everything she does is taken as a joke. Only Tiffany seems to realize there’s real hurt there, a nice callback to the renewed closeness of their relationship.
The women pull over at a liquor store to buy some drinks to sneak into the event. Issa, Molly, and Cheyenne are held up by a guy with a gun on the way out. As Molly and Issa hand over their valuables, Cheynne dissolves into hysterics so over the top that the gunman slips up and calls her “Chey.” Issa and Molly realize that Cheyenne is a co-conspirator in the robbery. Found out, Cheyenne steals Molly’s shoes, tells Issa she can keep hers, and makes off with the loot. When they get back into the car with Tiffany and Kelli, they tell them Cheyenne robbed them, and the unreality of the situation finally breaks the tension between them. They laugh at their own fear and recount the events for their friends, snorting the whole way. When Issa asks why Cheyenne didn’t take her shoes too, Tiffany retorts, “Aww, you know why,” setting them all off again in another fit of laughter. The entire sequence is funny and ridiculous in the way only Insecure is, highlighting how much of the show’s magic comes down to the relationships between these women. At the core of the show, this isn’t about men or sex or marriage. It’s about friendships and the love within them.
At a diner the next day, the girls give Kelli a proper eulogy over pancakes that befits the impact she’s had on their lives, and Issa and Molly both agree to move forward. As everyone filters back to their real lives, Kelli rather ominously asks her podcast listeners what they would do if they knew the end was near.
Lawrence, who’s been conspicuously absent for the entirety of the episode, picks Issa up from the airport to drop her home. When they arrive, we finally get a resolution for the bombshell at the end of last season. Tearfully, Issa tells him that she’s had a chance to think, then trails off. Lawrence nods; he knows what’s coming, and his face says he’s been expecting it. As much as they love each other, they’re done. Condola’s pregnancy is too big a hurdle for them to overcome. Despite their best efforts to try again, it doesn’t look like it’s meant to be. At least for now. And with that, we’re one week closer to the end of Insecure.
Week’s Best Woot Woots
• “Stars can’t shine without darkness. That’s not not deep.” — Derek
• “God, we were fake back before we were back back. Chile, the jokes I laughed at that weren’t even funny!” — Kelli
• “Did we meet T-Pain yet? Nappy Boy ooh-eeee.” — Mirror Issa
• “Hey, photos on an app? Invent that shit. Call it Issagram.” — Issa
• “The present. No time like the …” — Issa
• “I forgot I hated her.” — Issa