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Issa Rae Insecure

Yvonne Oriji and Issa Rae in Insecure.

I didn’t know what to expect when I watched Issa Rae’s new HBO show Insecure. I was a fan of her show The Miasdaventures of an Awkward Black Girl when it initially came out on YouTube, but I found that the more endorsements it received, the less funny and authentic it became.

So, I was nervous when I heard about her HBO show. I wondered about how much autonomy Rae would have as a writer, and if the show would speak to me. However, five minutes into the first episode, all of my suspicions evaporated. As the show progressed, I kept asking myself, “How does she know my life?”

Insecure is set in present-day Los Angeles and her character, also named Issa, is a 29-year-old who just came through her “Saturn return” and is struggling in her romantic and professional life, as well as her place in the world. She is dealing with what it means to be a woman who is not only young, gifted and Black, but also navigating issues such as racial microagressions, lack of self-worth and sometimes just feeling downright insecure.

Issa works for a nonprofit organization that helps low-income children of color, yet somehow she ends up being one of the only non-white people on staff. She spends the majority of her workday listening to her white co-workers preach to her about the black experience while reaping the benefits of white privilege by holding positions of power within the organization. Meanwhile, she’s in a dead-end five-year relationship with an unmotivated boyfriend who seems to spend the entire day in sweats, eating cereal and watching YouTube videos. Issa finds herself resentful of her boyfriend, yet hesitant to leave him because she doesn’t know if she can actually do any better.

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My favorite character in the show is Issa’s best friend Molly, played by Yvonne Oriji. Molly is a beautiful, goal-oriented woman in corporate America who is steadily climbing up the financial ladder while her love life remains at a standstill. In one scene, Molly discusses how she’s sworn off black men for men of other races because “They know how to treat a woman,” only to be dumped by a Middle Eastern man that she was casually dating because he didn’t want a relationship.

Molly hates being single in L.A., complaining that if she acts too cool, she’s seen as not caring enough, but if she’s too into a guy, she’s viewed as being clingy. Meanwhile, she watches her less-motivated, less-attractive, racially-ambiguous co-worker get wifed up by her Black boyfriend at record speed. (*Cough*Jaime Foxx and Katie Holmes*cough*.)

Despite the drama, there is joy. Issa and Molly’s relationship is far from perfect, but they’re there for each other. Their friendship keeps each other sane in a world that tries to make them feel less-than. This is Black sisterhood at its core. Issa Rae’s Insecure is funny and relatable. I was able to see myself and my friends reflected in the characters. That’s what I call representation! If you haven’t watched it yet, don’t deprive yourself any longer, and watch it here.

The second episode of Insecure airs this Sunday, Oct. 16, on HBO.


Heather was born in Chicago and raised in Pasadena, California and proudly claims Oakland as her adopted home. She has a B.A. in African-American Studies from Smith College (proud Smithie), and a Masters in Education Leadership from New York University. Heather's spent the past decade working in the field of educational equity and advocacy. She currently teaches Child and Adolescent Development at San Francisco State University and manages a blog called What's Happening Black Oakland? She also contributes to Blavity, a blog for black millennials. Heather's committed to writing interesting and relevant stories that aren't being covered by the mainstream media, while straying away from the single story that is usually imposed on people of color. In her free time she enjoys traveling and going to live shows.

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