Why Black Twenty-Something Women Need Issa Rae’s “Insecure”

I got hip to Issa Rae in my third year of undergrad, when my Fictions of Black Identity professor listed her web series, The Misadventures of Awkward Black Girl, as a potential text for final papers. Thrilled by the chance to write about YouTube as a medium (I’d recently spent an entire summer devotedly watching Vlogbrothers, Grace Helbig, and Hannah Hart) and intrigued by the title (wasn’t I an awkward Black girl that often engaged in misadventures?), producer, writer and actress, Issa Rae, quickly became the focal point of one my best papers to date– and a mild obsession. As a writer, she was inspirational– the content of her episodes are sharp, witty, and hilarious, while also hitting racial and social issues on the head in an accessible way. As an actress, her portrayal of protagonist “J” was relatable and oh so awkward. After watching J navigate a semi-hostile, micro-aggressive work environment, a blatantly evil co-worker, and an interracial relationship, while learning to feel secure in her own racial identity, I needed more.

Thankfully, Issa Rae is not only a creative genius, but also has a work ethic that allowed her to produce a humorous biography named after her web series, and most importantly, the HBO television series, Insecure, in the span of about two years. Insecure, like her web series, stars Rae as the protagonist, a twenty-something-year old named Issa, navigating a fairly unfulfilling job, a long term relationship with her boyfriend, Lawrence, that is sputtering to an end, and a close friendship with career-slaying lawyer, Molly, which is a source of comfort, envy and a lot of discomfort. If Awkward Black Girl offered more nuanced representations of Blackness than what are often seen in television and film, Insecure picks up and adds on to where ABG left off.

Instead of an interracial relationship, Rae spends her time developing a relationship between two Black people who are well past the honeymoon phase and are milling around in the zone of comfortable cohabitation, which pushes past the “Black love” romantic impulse of late 1990s and 2000s Black romantic comedies, like Brown Sugar and Love and Basketball. Instead of asking how do we find love, she instead asks: What does love look like once we’ve found it? Can we continue to grow individually once we’ve invested in growing together with someone? Can you grow individually and mutually at the same time, and if not, does that mean it’s time to move on?


Instead of focusing on a friendship bred in an office between an awkward Black girl and an awkward Indian girl, Issa Rae places Black woman-to-woman relationships at the center of her HBO series. Relationships between Black women have always been under fire, from family members who tell me that his or her Black female friends are nothing but drama, to the television shows that depict us as only being able to interact in a fight over a man–but Rae shows on television what I’ve come to know as true: Black women can be multi-dimensional and they can be supportive friends. Molly and Issa’s relationship is painfully relatable for me as a twenty-something-year-old girl with a lot of a relatively successful and happy Black female friends. I, like Issa, have been in awe and somewhat jealous of friends with Molly’s ease of inhabiting both Black and white spaces; I, like Molly, have wondered why I can’t find Issa’s “Black love” that a few of my friends have stumbled upon; and I, like both of them, have benefited from and been distressed by friends who are a little too honest, but always with your best interest at heart.

Most importantly, Issa Rae’s Insecure shows what it’s like to just be, to simply exist as a Black girl, just kicking it in this world, comfortably inhabiting whatever identities seem to fit, without feeling like other identities compromise what each of them individually feel Blackness is for them. Much like the 2000s’ Girlfriends and the 1990s Living Single, Issa Rae’s show Insecure is operating in a lineage of shows about Black women being unapologetically themselves and living their best lives. Issa Rae’s characters are by no means perfect– in fact they are deeply messy: Issa is self-absorbed to the point that she can’t adequately assess and appreciate her partner’s ambition and goals, a fact that certainly aids in the destruction of the relationship, and Molly flits from fling to fling, so enchanted by the idea of a perfect, true love, that when she meets someone who’s lacking in a few of her “must-have’s,” she’s unwilling to even investigate it.

There’s nothing wrong with introspection and self-reflection, or an investment in true love, but as Rae shows, realistically, those traits can sometimes have unintended consequences. Her characters are real and messy, and you see your good traits reflected on the screen…and the bad.

She shows us that it’s okay to be twenty-something with a dead-end career. It’s okay to be twenty something with no-career. It’s okay to try again. It’s okay to love and excel at your dream job. It’s okay to reassess. It’s okay to grow, with or without people. It’s okay to indulge in your desire for love. It’s okay to indulge in yourself.

I, for one, spend more time than I’m willing to admit, making sure that I’m meeting expectations. Insecure reminds me that the only expectations I need to meet are my own. I’m growing. I’m learning. And it’s okay to just be me…even if I am still a work in progress.

Be sure to check out Issa Rae’s Insecure on HBO Go. (If you sign up for free trial you can watch the whole show for free and then cancel your subscription.)

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