What the HBO Dramedy ‘Insecure’ Means To Me

I adore the dramedy “Insecure” on HBO. The television series means more to me than just your run-of-the-mill TV pastime. The show validates my Black woman experience in a manner that I have never seen on television in my 36-years of life. Prior to Insecure’s entry into the TV-Universe, I felt disconnected from TV characters. They never had the same flaws and idiosyncrasies that I embodied.

Growing Up As a TV-Sitcom Fanatic

As a child, I was a TV-sitcom fanatic. Saved By The Bell, Clarissa Explains It All, Family Matters, Step By Step, Moesha, Parkers, and Cosby Show were some of my favorites. While I appreciated the characters, I didn’t feel that they truly represented my unique level of awkwardness. I wasn’t as fashion-forward and popular as Lisa Turtle on Saved By The Bell. Clarissa was as smart as me, but she embodied a level of confidence that I could only aspire to be on Clarissa Explains It All. Laura Winslow and Moesha were the ultimate triple-threat characters on Family Matters and Moesha, respectively: smart and popular and assertive. The bonus was that they had boys swooning over them. I was smart, but I was unpopular and rather timid in elementary school. Boys were not checking for me in middle and high school.

While I appreciated the characters in Family Matters, Saved By The Bell, Moesha, and The Parkers, none of the characters represented my unique level of awkwardness.

The trend persisted in other shows until I was in my sophomore year in high school. In 2000, Love & Basketball was released and although I wasn’t an athlete, I could identify with the awkwardness of Monica Wright. She preferred to wear a jersey than an apron. She stumbled to walk in high heel shoes. It was difficult for her to hold a conversation with a guy. I could tell that she was rather uncomfortable in her skin and because of that, I saw myself in the character. Today, Love & Basketball remains one of my all-time favorite movies and Monica Wright is one of my all-time favorite movie characters.

Awkward Black Girl

I discovered Insecure’s predecessor, Awkward Black Girl (ABG), in 2012. I was having a tough time navigating the job market. I was underemployed, working as an office assistant at a life insurance company. At that time, I had an advanced degree in public health. My friend introduced me to the web series on YouTube. The shows were short and funny. I was amused at how funny and relatable the ABG stories were. J (ABG character) was generally uncomfortable in her skin and as she attempted to navigate everyday life, she could not get away from the fact that she was awkward.

I discovered Insecure’s predecessor, Awkward Black Girl (ABG), in 2012. I was having a tough time navigating the job market.


Pivotal Moment – Insecure was released on TV at a pivotal moment in my life. I had recently turned 31; relocated from Atlanta, GA to Greensboro, NC; completed my second master’s degree; and I was navigating my insecurities while trying to land a new job in a new industry and in a new city. My husband and I had gotten married a few months prior and we were living in separate cities. My life was at a crossroads, as I was trying to figure out where I wanted to live, where I wanted to work, and how my husband and I were going to merge our lives together.

Insecure was released at a pivotal moment in my life. I found a lot of myself in Insecure’s main character, Issa Dee.

Relatable Content – I found a lot of myself in Insecure’s main character, Issa Dee. Issa was also trying to sort out a long-term relationship with her boyfriend, Lawrence and trying to manage micro-aggressions from her White co-workers in the office. She was smart, held a bachelor’s degree from a prestigious university, yet often struggled to find her own voice. To express herself, she rapped about her thoughts, emotions, or uncertainties in the mirror. She had an off-beat sense of humor. During conflicts, she hardly articulated her true thoughts and emotions. Instead, she would manage her angst internally, channeling that bottled-up energy in her rap lyrics or vivid daydreams.

I was smart, held multiple fancy degrees, yet I never felt comfortable enough in my skin to speak my truth

Life Imitates Art – I grew up in a predominately white suburb, worked in predominately white environments, and had encountered a lion’s share of microaggressions through grade school and in the workplace. I was smart, held multiple fancy degrees, yet I never felt comfortable enough in my skin to speak my truth. I often spoke aloud to myself (not in a mirror) about my frustrations, insecurities, or overall opinions that I was too timid to express in front of people. I often felt like few people knew the real me because I never expressed myself authentically. I also had a corny sense of humor and was adept at avoiding conflicts, resorting to my own internal dialogue to process my emotions.

Friendship – It was refreshing to see Issa Dee navigate her work and personal life, particularly her relationship with her best friend, Molly, and the ladies in her friend group, Kelli and Tiffany. I had my own close-knit friend group and could relate to the ups and downs and occasional conflicts that came from our dynamic. Throughout Insecure’s 5-year run, Issa Dee broke up with her boyfriend, attempted to navigate the dating scene in the 2010’s, encountered financial difficulties, quit her non-profit job, moved to a new apartment, supported her Tiffany as she became a first-time mom, and embarked on new serious relationships, participated in multiple girl trips and outings and most importantly, she learned to settle with her own insecurities.

Issa Dee’s Story in Parallel to Mine – I am thankful to this show for entering my life in my early thirties. Issa’s onscreen life paralleled my offscreen life, as I settled into married life, supported my friends as they embarked on their journey into motherhood, and started my new career in healthcare informatics. Along the way, I relied on my blog to be my form of expression. I learned how to be secure in my own insecurities and speak my truth to others around me.

It has been 5 years since the show’s release and I feel that I am the most authentic version of myself. It’s nice that I did not have to navigate through my complex journey alone. I had Issa and Molly on that same journey as well. Moreover, these women looked like me, so while they were portraying universal situations, they were doing it in a manner that felt authentic to me as a Black girl.

Cultural Icon – The show often depicted my Black experience. We heard Wipe Me Down play at Kelli’s birthday party in Season 1. We heard Case of The Ex play in Season 4 and I Luv You Girl in Season 5. These songs helped me recall a simpler time in my life. There were also throwaway lines scattered throughout the series the spoke to the little Black Girl in me, such as Molly’s reference to the Beyonce’s outfit in Check On It in Season 2 and the portrayal of modern-day Black church in Season 3. Moreover, Issa had naturally kinky hair like me. Each week, she would show me the possibilities of natural hairstyles.

The show is a Black cultural icon. The show reflected Black people’s nuanced reality. Reflecting on 5 seasons of Insecure, here are the moments that I found the most relatable to my life.

Times When Insecure Closely Resembled My Life

  1. Season 5, Episode 1 – Reunited, Okay?!

Issa is looking at herself in a restroom mirror at her alma mater, Stanford University when a young version of herself appears in the mirror before her. Young Issa wants to know how her life turned out and asks Issa a question while using the slang  that I’m ashamed to admit that I used back in 2005,

“Are you and Molly still gully fo shizzle?”

2. Season 2, Episode 3 – Hella Open

Meeting Men – Molly takes Issa out to a club, so that she could meet new people following Issa’s breakup with Lawrence. Issa, the forever awkward black girl, doesn’t know how to talk to men, so she says to the guy sitting to next to her at the bar, “I bet you’re really good with your drill.” The guy, who is clearly turned off by the comment, puts his cell phone to his ear, walks away, leaving Issa at the bar by herself.

As for me, I cannot tell you how many times men have excused themselves from talking with me at a club or bar, simply because the conversation was so uncomfortable, they needed to leave.

Awkward Sex Scene – This episode also gives the most awkward sex scene in TV history. Issa visits Eddie, her neighbor. They watch Gossip Girl reruns and Issa kisses him. Next thing you know, Issa kisses him and they start to remove each other’s clothes. The problem is that Issa has on tapered jeans, so she and Eddie struggle to remove them. They try various positions, with Issa’s head on his headboard, which gave me crick in my neck when I looked at it. The scene lasts for 1 minute and 4 secs and I cringed for all 64 seconds. The love scene reflected a reality that no one talks about. Sex is not always as seamless as TV makes it look.

Y’all got to see it. Turn to your HBO Max App, click on 23:37 to 25:01 on Hella Open in Season 2.

3. Season 2, Episode 2 – Hella Questions / Season 3 – Episode 7, Obsessed-Like

Stalking The Other Woman – Both episodes show Issa engaging in cyber-stalking tactics that’s both comedic and cringe-inducing. As someone who is an expert at conducting *ahem* Internet research *ahem* I felt triggered at how accurately, Issa Rae portrayed my obsessive online-stalking tendencies. The amount of investigations that I have done on Facebook, Instagram, LinkedIn, and even on random sites I stumbled upon at Google to find information on a crush or my ex’s new boo is quite embarrassing.

Being Ghosted – In Obsessed-Like, Issa is ghosted by Nathan. As she tries to navigate through the experience, her inner thoughts about why he ghosted was painfully authentic. Negative self-talk is my specialty, especially when someone leaves without warning. Nathan was Issa’s cheerleader and encouraged her to openly share about her family life, her childhood, and even divulge weird facts about camels. Nathan was intrigued by her backstory and knowledge, yet Issa points to these facts as the reason why Nathan is not responding to her phone calls, text messages, and other attempts to contact him.

4. Season 4: Issa and Molly’s Friendship Breakup

Season 4 shows the breakdown of Issa and Molly’s friendship. It starts with a series of poor communication, tension accumulates over time. Eventually, the two have an explosive argument at Issa’s Block Party in Episode 5. Back-handed insults and compliments were plentiful in Season 4. Following one final argument with her bestie in Episode 9, Issa sobs when she enters the Lyft.

I felt that on a very personal level. I endured a friendship break-up in 2014 that I just recently processed. I am currently adjusting to friendship adjustments right now. It hurts. The show brought a level of accuracy and honesty to friendship breakups that I have never seen onscreen. They normally happen gradually and over time, you and your friend grow apart.

Insecure has been a form of therapy for me. It’s been aspirational, as I embark on a new chapter in my life and cultivate new friendships and re-evaluate current ones. The show brought me laughs and one-liners. It made me cry. It helped me appreciate Black culture in a new way and become re-acquainted with Los Angeles. I have traveled to Los Angeles many times, yet the show helped me see the city through a new lens. I have a running list of places that were featured on the show that I want to visit in South LA. Most importantly, Insecure helped me see myself in a way that I have never seen before: my flaws, my idiocyncrasies. It showed that it was okay to be professionally thriving, but still have flaws. I will forever cherish its moments. I am eternally grateful to Issa Rae, HBO, and the rest of the Insecure team for making me feel seen.

Photo is courtesy of HBO and Deadline.

3 thoughts on “What the HBO Dramedy ‘Insecure’ Means To Me

  1. My sentiments exactly! This show and its characters resonated with me on multiple levels. Sad to see it go but grateful to have witnessed the greatness is my lifetime. Insecure will forever be embedded within my heart ❤. Oh I’m also a Cali girl so ya know!! Issa Dee and Rae did that!!!!


  2. My sentiments exactly. This show and its characters resonated with me on multiple levels. I’m sad that it has come to and end but grateful to have witnessed this greatness in my lifetime. Insecure will forever be embedded within my heart ❤ Oh and I’m a Cali girl too just like Issa Dee and Rae! So ya know!!


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