Television

Insecure Had One Last Trick Up Its Sleeve

A sometimes frustrating final season comes to a surprisingly satisfying conclusion.

Yvonne Orji and Issa Rae on Insecure.
Yvonne Orji and Issa Rae on Insecure. Merie Wallace/HBO

Insecure has always dealt with magic: the magic of music, of various sorts of contraband (from alcohol to, in one of its best episodes, something a bit more hardcore), of love and sex, and, of course, #BlackGirlMagic. But the most magical thing about Insecure is that through its ups and downs, it’s been both so singular that it has launched truly cutthroat debates on Twitter and amongst your friends at the function, and so familiar that it feels like giving your girls the lowdown on a Tuesday evening FaceTime call. Insecure feels like Tuesday. How do you write about Tuesday, especially when it’s the last one you’ll ever have?

Advertisement

I guess you start by acknowledging that although Tuesdays are fundamental, they’re not always great. I had never seen anything like Insecure when it first premiered in 2016. I was newly 20 and had yet to experience an adult life beyond a college campus that, like the show, would include consoling friends through the ends of meant-to-last relationships and, you know, legal drinks at bars. From Insecure’s inception, when it was still just creator Issa Rae’s popular YouTube series The Mis-Adventures of Awkward Black Girl, it felt like a breath of fresh air: Here was a funny and cringe-worthy, relatable Black girl who felt like all of us at our best and definitely worst moments. The landmark Black HBO dramedy show that arose from the ashes of YouTube exceptionalism filled a void for Black viewers, particularly Black female viewers—they couldn’t tell how badly they needed the show until they had it. Insecure was hilarious, stylish, and (or so I’m told) hella L.A. From the costuming to the locations and the music, Insecure had figured out something the TV industry had been trying to get since the days of Living Single and Girlfriends: How do we make a deeply human show about the experiences of a young Black woman in the age of the internet? The answer: move beyond the classic multi-cam sitcom to show not just age or work or dating, but also place. Ground it enough that it feels inextricably built by Black culture, while simultaneously defining Black culture—another magic trick.

Advertisement
Advertisement
Advertisement
Advertisement
Advertisement

However, as I said, not all Tuesdays are great: Season 3 is disappointing, although it laid the groundwork for Season 4, which I consider to be the uncontested best season of the show. Insecure’s bread and butter has always been its friendships, the female friendships: the way women support other women and how easily decades of friendship can become unraveled until they’re an unrecognizable mess. And in that unrecognizable mess, the holes that are left that only your girls can fill. When Season 4 aired after a two-year hiatus, every single Insecure fan I know felt at home again, rightfully saying that the show had gotten back to its DNA and proved, once more, why it’s one of the best television shows of the 2010s. The festering feud between Issa and Molly is an absolute marvel of television, perfectly paced with the right balance of hilarity and heartbreak. It’s the most relatable (and definitely the most debatable) the show has ever been.

Advertisement

And then there’s this fifth season, the show’s last. [Spoilers for Insecure’s series finale follow.] Honestly, this season has been a bit of a rough battle; it’s had some remarkable highlights, like depicting the way Molly balances a family emergency and work, or any and every moment with Kelli. But it’s also felt inconsistent and elusive throughout. Issa begins to build a relationship with Nathan again, who (sorry not sorry) is the least interesting character the show has drummed up, mostly because he is treated as Issa’s counterpart rather than his own full character, something the show attempted to rectify in its last season but didn’t quite achieve. Molly is in and out, dating sometimes, until she finally settles down in a lovely surprise turn with work frenemy Taurean in the final few episodes. Tiffany is mostly absent until she announces she’s moving to Denver, which is the first real sign that the heart of the series might fundamentally change. And there’s not enough Kelli or Ahmal, Issa’s hilarious brother, though there historically never is.

Advertisement
Advertisement
Advertisement
Advertisement

It isn’t until the final few episodes that Season 5 really launches into gear. By the end of the season, Issa has some vital decisions to make: Nathan or Lawrence; “selling out” with NBW and the corporate life or keeping it local with Crenshawn. Is continuing with the Blocc even the right path for her? At the end of this five-season journey, the main character who has been notoriously indecisive and, as her loved ones point out in the final episodes, “inconsistent,” must choose.

But, spoiler alert: Issa decides she wants it all. Issa has kept herself from settling down romantically or choosing a right path for her career because she’s built up this idea in her head that she couldn’t have everything, that she must choose. It wasn’t only that she couldn’t have everything, but that she always owed something of herself to other people: to be a better friend to Molly, a support system for Lawrence, to stay true to her community. It isn’t until the final episodes that the truth comes at Issa from all sides. ”Sometimes it’s not about making the smart choice, it just has to make sense to you. And it doesn’t have to be the smart choice to be the right choice,” Tiffany tells her. In the next episode, Molly asks, “What if there’s no wrong answer? Things are never all or nothing.”

Advertisement
Advertisement
Advertisement

Issa chooses the Crenshawn career path, continuing to uplift the community. But she also finds the money to open up a new space for her company, suggesting that she may have also partnered with NBW to get a payday. Issa chooses to stay close to her girls and to progress at work, managing to fulfill their pact of being there for each other’s birthdays. And, at the end of it all, after a long and bumpy road Issa chooses Lawrence. They take comfort in knowing that they needed to grow separately to be able to work as a couple, but their relationship was never truly off the table. Issa’s infidelity was a result of her trying to create a perfect relationship that didn’t exist. “I realized it was all in my head,” Issa says in the finale. “No one was doubting me except for me… I had to believe that it would work out for it to work.”

Advertisement
Advertisement

There’s a brief dream sequence in the Season 2 finale when Issa and Lawrence finally get the closure they need and say goodbye to each other. It’s devastating when the dream is cut short, to see Issa realize that her dreams would never come true, at least not the way she imagined them. Being #TeamLawrence or #TeamIssa back in the day was a strong statement, but no one could deny that dream felt right. And that dream isn’t far from the reality we actually receive. I’m not going to say that the ending of the series isn’t fan service, because it is. But it doesn’t feel unearned, and it doesn’t feel unbelievable.

The point Insecure’s final episode makes is that Issa never had to choose. Even when it seemed like Issa’s actions were in service of her greediness, they weren’t. She didn’t have to choose between, she could choose in addition to, as long as she was honest about her choices and what she wanted out of them.

Advertisement

I expected to be dissatisfied with the finale, perhaps because this season has been a tug-of-war between the values at the heart of the show and a drawn out pause to leave us lingering on the question of how it all ends. But honestly, I’m so tired of the narrative of the girl who doesn’t choose between the two men and instead melodramatically chooses herself. Why can’t she have both love and personal growth? Lasting friendships and a commitment to work, a career, in any form she wants it? Insecure says she can. She always could. She just had to believe she could make it work. And that, to me, is the greatest rabbit Insecure could ever pull out of the hat. Damn, am I gonna miss Tuesdays.

Advertisement