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A Love Letter to ‘Insecure’

A Love Letter to ‘Insecure’

Written By: Angelica Monk

Sunday’s finale of HBO’s hit series, Insecure, was the end of an era. 

Every so often a series comes along that defines a generation and Insecure was it. Never has the experience of a young, Black millennial been portrayed so beautifully. 

Issa made me feel seen, in more ways than one. The idea of Black people existing was such a revolutionary concept. I can think of very few shows centered around the Black experience that doesn’t exploit Black trauma. Insecure found a way to give us light. Heartbreaks, friendships, failures, and the uncertainty of the future was lovingly crafted through the eyes of strong Black women. They were humanized and flawed — that’s what made the show so relatable. 

How many of us had a boyfriend that was “project” and never met his real potential? How many of us had a best friend who seemingly had it all, making us feel inferior, or a job that paid the bills but we hated? These were the stories that Issa brought into our homes every Sunday night with her trademark quirky flair.

I can’t remember how many times I have sat in my circle of friends and thought, “Which one of us is Issa, Molly, Kelli, or Tiffany?” A representation of a diverse group of women all beautiful and successful was something I had never seen on screen. These were all college-educated women who effortlessly switched between Standard American English and AAVE. I will never forget Issa’s exchanges with Mirror Bitch, the absolute highlight of the show. For the first time in my adult life, I saw people who talked and acted just like me! 

Not only did they sound like me, but they looked like me too. Issa was a naturalista with hair that was to die for. Each week I looked forward to seeing her hair in braids, curls, a twist out — anything to draw inspiration for my everyday life. And let’s get into the fashions. That Molly was sharp! I found myself googling her looks for some fabulous blouse that I could wear in the office (pre-pandemic of course). Don’t get it twisted — Issa, Kelli, and Tiffany brought it too. Til this day, I’ve been stalking Telfar’s website with my eye on that sage green shopping bag that Issa was rocking in Season 5’s premiere. Please take all my coins.

We can’t talk about Insecure without talking about the music. Each season the soundtrack was fire. Whether we were nodding along to Keli’s Bossy or Issa’s “cypher” of “Broken P*ssy,” Goldlink’s “Palm Trees,” “Run Up” by Cam & China, “The Glow” by Victoria Monet, or Teamarr’s “Temperature,” the music set the tone for the inevitable cultural time capsule that is the show. Insecure does not miss, I find myself bopping my head every episode and adding new songs to my playlist. 

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On top of the music, the cinematography was breathtaking, an ode to Los Angeles. The show did not shy away from showing parts of LA that many would fear to venture into. It is refreshing to look beyond the glitz and glam of Rodeo Drive, Sunset Boulevard, or the Hollywood Walk of Fame. We see the Ethiopian Merkato, Leimert Park Village, Mavericks Flat, and the now iconic Dunes — I plan on making a pilgrimage to this location on my next visit to LA, forgot about the Hollywood sign.

Insecure was instrumental in shaping my late 20s and early 30s. When Issa quit We Got Y’all, I found myself at a new organization ready to start a new chapter. When Molly was going from one failed relationship to another, I found myself doing the same. No one seemed to stick, and like Molly, I started to question my self-worth. I saw Kelly and Tiffany struggle in their friendships and to a greater degree Issa and Molly; I looked within and discovered I need to work on my friendships as well. I think we could all relate to Issa’s longtime love for Lawrence. How many times have we tried to work it out with someone, and it never felt right? Yet somehow, our hearts yearned for them and instead of dealing with ourselves, we pour into another person (looking at you, Nanceford). Like Issa, I eventually got it together with the men in my life but not before I dealt with myself. “You know what that is? Growth.”


Speaking of men, I can confidently say Insecure wasn’t just about Black women; it also brought a level of care and sensitivity to the plight of Black men. Whether it was Lawrence tackling his ambitions (or lack thereof) and the realities of co-parenting or Nathan finding balance with his love life and mental health, these men were portrayed with such grace. Nearly all my guy friends were just as invested in Insecure as I was. They saw themselves just as I saw myself. Whether you were Team Lawrence or Team Nathan, we all loved Insecure.

The last five seasons have given me so much joy, I don’t know if anything will compare. Insecure has ushered in a new wave of shows portraying the Black experience. We now have Harlem, Run the World, and Sistas. I can’t help but think they were all made possible because of an Awkward Black Girl. I will wholeheartedly miss Insecure Sundays, but I will always be grateful to Issa Rae for bringing this series to life. Always…okay?

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