By Terrance Turner
Dec. 26, 2021
This recap contains spoilers.
Tonight was the final episode of Issa Rae’s groundbreaking HBO series “Insecure”. In a chaotic, jam-packed finale that stuffed two hours of content into 40 minutes, (almost) everyone somehow ends up on the path they wanted. Issa Rae’s remarkable screenplay centered around birthdays — each finding the characters in a slightly different place than before. Throughout, lead character Issa Dee is faced with the choice of whether to pursue what makes her happy.
The episode begins by addressing the fallout from last week’s episode, when a going-away party for Issa’s friends turned into a battle royale. Simmering tension between Issa’s boyfriend Nathan (Kendrick Sampson) and her ex Lawrence (Jay Ellis) exploded when the two came to blows and had to be separated. The brawl was prompted by Lawrence’s game-changing confession: “I realize that I am not happy when I’m not with you. Because…I love you, Issa.”
On the drive home from the party, the awkward silence holds a heavy weight between Issa and Nathan. Issa invites him inside to talk, but Nathan gently rebuffs her: “I don’t really have nothing to say.” He’s not interested in trying to talk things out. “This ain’t good for me,” Nathan says, adding that the fight was “embarrassing”.
“I gotta take a step back. This messy shit is just…toxic to me,” he tells Issa. “I’m good.”
“OK,” Issa answers. She understands.
Issa gets out of the car, goes inside, and wakes up the next morning in the same dress she had on the night before. Her best friend Molly shows up to bring food and support, but Issa is dejected. “I’m gonna go take a shower,” she mumbles.
While looking in the bathroom mirror, Issa faces inner doubts and harshly critical self-talk. Issa’s reflection (whom she calls “Mirror Bitch”) tears her down: “You’re down bad. I don’t know where you go from here.” She adds: “You was trippin’ about all those decisions and choices, just to end up here. You hate to see it!”
Issa looks in the mirror with huge, expressive eyes that convey her feelings of sadness and defeat. “I just wanna fast-forward to the part of my life when everything’s OK,” she says.
“Good luck, champ,” Mirror Bitch sarcastically responds.
Cut to Molly’s birthday party, where we learn that Issa and Molly’s mutual friend Kelli (Natasha Rothwell) is newly taken, with a gorgeous new man named Desmond. (Though the chart included here says Molly is a Scorpio, we learn in a previous episode that Molly’s birthday is August 13.) It’s unclear how Kelli met Desmond, although the two seem happy. Mutual friend Tiffany (whose going-away party was marred by the fight) mistakenly remarks that all her friends are “boo’ed up” — except for Issa.
When Tiffany (Amanda Seales) realizes her mistake, Issa plays her single status off as no big deal. “It’s fine,” she pretends. Issa goes to check on Molly, who’s having difficulty deciding what to wear. She helps Molly pick out an outfit (which she ends up changing anyway). Molly emerges, looking great, and is greeted by friends and family singing “Happy Birthday”. The birthday party (which Issa planned) is a success; Kelli congratulates Issa for doing a good job. But Issa doesn’t seem to believe her.
We flash ahead to Issa’s birthday (in December or January?), at a surprise party that Molly and Issa’s assistant put together. We see her and her friends picking out potential men for the night. While Issa tries to chat up a prospect, Kelli says she has to get back to work: “The white man got me on a deadline.” Molly points out that she’s talked to her Black-owned law firm and that they’re willing to open an estate division. (Kelli helped Molly’s parents with estate planning and had indicated that she wants to do more work in that realm.) After some convincing, Kelli agrees. She’ll call Molly in the morning.
Then Nathan shows up to give Issa a card on behalf of the barbershop where he works. “We wanted to donate since you were so helpful to us,” he says. They make pleasant small talk and seem cordial, but it’s clear that things are over.
“How have things been with you?” Issa asks.
“Good,” Nathan answers. “This place is finally starting to feel like home.”
“Really?” Issa asks, visibly stung. “I’m really happy to hear that.”
“I always thought people come into your life for a reason, and you have made up so many good reasons for me,” she tells Nathan. “I just hope you didn’t regret anything.”
“I don’t,” he answers. They say goodbye.
We skip ahead to Tiffany’s birthday (around September, the next year?). The ladies fly out to Denver to visit her and learn that Tiffany hates Denver: “I’m so glad you guys came,’ she says. ‘I f–king hate it here.”
“I don’t know anybody; I’m still not working,” Tiffany complains. “I didn’t come here to be a Real Housewife of Denver.” Tiffany adds that Derek’s parents aren’t as involved as before, and her daughter Simone is the only black girl in her class. Then she deflects her unhappiness and asks how the other girls are doing.
During this outdoor convo, we also learn that Issa has a new man (though she swears “it’s not like that”.) She met Nasir at an event she did with Crenshawn. She shows her friends a picture of Nasir; they approve. But Issa seems…unsettled. While in the house, Issa is happily pouring wine when she notices a picture of Derek and his friends with their kids…and there’s Lawrence. Even though nearly a year has passed, Lawrence is (literally) still in the picture.
Molly asks what many fans have likely wondered: “What would you have said to Lawrence if Nathan hadn’t interrupted?” Issa doesn’t have an answer, but insists that “it’s too late anyway.”
“Girl, it’s not too late if that’s what you really want,” Molly tells her. And then she gets a call…
Issa later calls Lawrence — on his birthday. (Apparently he’s a Cancer, so this is in June or July the next year.) After making some awkward small talk, she gets to the real. “I’ve been thinking a lot about things…about you,” she begins. “So I guess I’m calling to see if I could take you out on your birthday.” Lawrence already has plans (with another woman). But he’s open to dinner in the future.
Out of nowhere, at Kelli’s birthday (late July, early August?), we learn that Kelli is expecting a baby…with Desmond. Tiffany’s elated. Issa is surprised, since Kelli had earlier indicated that she didn’t want kids. “I would not, under any circumstances, do this with anybody else,” Kelli says. “I don’t want just any n–ga’s kids. I want this n–ga’s kids.” (That’s just one of several curveballs throughout the episode: each character’s story line has surprises up its sleeve.) Issa is happy for Kelli — or wants to be. But it’s another reminder that everyone seems to be progressing but her.
Later, we see Issa in the mirror, getting ready for a boudoir appointment with Nasir. “Everybody is making moves and getting what they want, and we’re on that path too!” Mirror Bitch enthuses. “Yeah, it’s great,” Issa says, unconvincingly. She reaches out to Molly, but the call goes to voicemail. (Molly is still grieving the loss of her mother, which she learned of while in Denver.)
In the middle of all this, Lawrence calls. Mirror Bitch screams at Issa not to pick up. “Don’t answer!”
“Why not?” Issa asks.
“Because it’s never gonna work, you dumb bitch! Move on!”
Issa calls Molly on her birthday (August 13) and they catch up. Molly is at work in her office; Issa is also in an office, having finally gotten office space for her company. Issa asks how Molly’s doing; Molly laments the fact that this is her first birthday without her mom. Issa reminds her that it’s OK not to be OK.
Issa invites Lawrence to her new office, which she’s secured for her company, The BLOCC. She takes him on a tour of her (minimal) new digs, planning out where the office kitchen and lounge areas will be. It’s not much of a tour, but that’s not the point: after a season that began with her not remembering the acronym for her own company, Issa finally has a company office. Issa reflects on her hard-won progress.
“I keep thinking about all it took to get here: doubting myself, going back and forth about what I wanted, being scared to waste my time and look stupid, in case none of it worked out. And then I realized…it was all in my head, you know? No one was doubting me except for me.Issa Dee
Issa concludes this stirring speech with words that apply both to her growing business and her relationship with Lawrence: “I had to believe that it would work out for it to work.”
“So do you believe it’ll work out?” Lawrence asks. Issa responds:
“I’m okay with finding out.”
The timeline then skips ahead a year, which finds Issa celebrating in a very different place. Smartly clad in a red power suit, she’s instructing her staff at her now-complete office for the BLOCC. The company has a clear mission/vision statement and several upcoming events. (Note the posters on the wall of The BLOCC, one of which features an event sponsored by NBW.)
Suffice to say that Issa gets everything she wanted — just in a different way than she imagined.