How “Chicago Boy” By Ari Lennox Made Me Remember That I Used To Be Awkward 


How “Chicago Boy” By Ari Lennox Made Me Remember That I Used To Be Awkward 

Many of the ladies that reached young adulthood in the early 21st century grew up hearing their mothers listening to artists like Erykah Badu and Angie Stone. Some of those ladies eventually became artists themselves and picked up the mic to continue to deliver the neo-soul sound, but with even more bluntness. Artists like Summer Walker, Janelle Monáe, and a personal favorite of mine,  Ari Lennox. 

In 2016 during press for her debut EP, “Pho”, Ari Lennox stated, “Sometimes women are put in this box where we’re only supposed to talk about certain things, I want to be braver and riskier. I think people want to hear that kind of honesty and frankness.” 

Three years later, Ari opened her debut full length studio album, Shea Butter Baby with the song, “Chicago Boy”. The songs starts off with the melodic sound of a trumpet playing softly, then Lennox goes into telling a story about meeting an attractive guy on a trip to CVS and wanting to get closer than close to him. 

She sings “Said listen, baby / I know that I’m speedin’ up this vibe / Is you gon’ judge me / If I fuck you ‘fore I catch this flight?” on the hook. 

As a bashful guy that takes awhile to open up to someone, the boldness and assertiveness that Ari Lennox brought on “Chicago Boy” as she made the first move was refreshing to hear. I have always found it really attractive when a woman go against society’s norm and make the first move. In a world of women with communication issues and insecurities, straightforward and confident women are always a plus. 

Don’t get me wrong, I have never been afraid of shooting my shot. I have never been agitated of missing neither. Sometimes it’s just a problem to initiate the conversation. Being an introvert, it has always taken me a while to build up the nerves and stop the procrastination. Getting out of my own way and stepping out of my laidback shell was always a challenge. 

In the summer of 2012, I was making plans to move away from my hometown of Aliceville, Alabama and attend school at the Art Institute of Atlanta. While doing a little research about the school, I came across the school’s official Facebook page. That’s when I came across a young lady that caught my eye who was currently attending the school. Her name was Chanel. Chanel was beautiful with an angelic smile. She had a light complexion, plump cheeks, plump pink lips, and plump everything else. I hit the “add friend” button on Facebook faster than contestants hit that button with their one hand on Family Feud.   

We became Facebook friends and started messaging each other just about every other day. That eventually turned into everyday. Talking about the school, talking about our hobbies, college majors, and all of that good stuff. She was into fashion and modeling. I was into photography. So the conversation was there. I was a country boy and she was a city girl. She taught me the ropes on a few things like “city slicks” and even walked me through riding the public transit via text message. 

Weeks after I had moved and started school, I still had not met Chanel. Even though I was eager to meet her, I was hesitant as well. Both shy and excited I guess you could say. Weeks and days had passed and we eventually made the plan to make it happen. 

We met at the main entrance of the school. This instantly became one of the most weirdest moments of my life. I would talk a lot while texting, but now that we were finally face to face, I turned into a complete mute. I never felt so shy and stupid in my life. If there was a fire alarm around, I definitely would have pulled it to run like hell. Honestly I was kind of star struck. Like wow. I have started a friendship with this beautiful girl that I thought was out of my league. And it actually seemed like she liked me. We stood there for maybe ten minutes and barely said ten words to each other. 

A few days later after we went our separate ways from meeting each other for the first time, Chanel was sure to let me know how she felt about my quietness. I don’t remember everything she exactly said, but I remember her using the word uncomfortable. 

My shyness had me being a procrastinator and a mute. My lack of self confidence had me skeptical and in a daze. This all happened at the age of 20. As I got older and matured, I built confidence through self-awareness. I believed in myself more and trusted that I was capable of more. Evening believing that I was able to get the most beautiful girl in the room if I wanted to. 

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