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 

A lot of women who came of age in the early 2000s didn’t just grow up—they were raised on a soundtrack. Their mothers had Erykah Badu floating through the house like incense, with Angie Stone laying down that grown-woman gospel about love, patience, and knowing your worth before somebody else tries to price it for you. That kind of upbringing doesn’t just shape taste—it shapes voice.

So naturally, some of those same women picked up the mic themselves. But instead of whispering around the truth, they walked right up to it, tapped it on the shoulder, and said, “Let’s talk.” Artists like Summer Walker, Janelle Monáe, and—one of my personal favorites—Ari Lennox didn’t just inherit neo-soul; they updated the firmware. Same groove, but now it speaks a little louder, a little bolder, and with a lot less sugarcoating.

Back in 2016, while introducing her debut EP Pho, Ari Lennox made it clear she wasn’t here to play polite. She said, “Sometimes women are put in this box where we’re only supposed to talk about certain things. I want to be braver and riskier.” Translation: the filter is optional, honesty is not.

Fast forward three years, and she opens her debut album Shea Butter Baby with “Chicago Boy”—a record that slides in smooth with a soft trumpet, then immediately gets comfortable being uncomfortable in the best way. It’s storytelling with intention. She meets a man at CVS—of all places—and instead of playing it coy, she leans into curiosity… and chemistry. When she sings, “Is you gon’ judge me if I f*** before I catch this flight…”, it’s not just a lyric—it’s a challenge to the listener, wrapped in velvet.

Now me? I’m the kind of man who can write a paragraph before I say a sentence. I take my time. I observe. I overthink like it’s a paid internship. So hearing that level of boldness—a woman stepping up, making the first move, owning her desire without apology—that was refreshing. That’s attractive. In a world where communication can feel like a game of charades, clarity is luxury. Confidence? Even better.

Don’t get it twisted—I’ve never been afraid to shoot my shot. Missing doesn’t bother me. It’s the loading screen that used to take forever. Starting the conversation? That was my boss battle. Being an introvert meant I spent a lot of time negotiating with myself before I ever spoke to anybody else. Stepping outside that laid-back shell wasn’t impossible—it just required a little internal pep talk… and sometimes a deadline.

Take the summer of 2012, for example. I was preparing to leave my hometown—Aliceville—and head to the Art Institute of Atlanta. While doing some light research (and by “research,” I mean scrolling with purpose), I landed on the school’s Facebook page. That’s where I saw her—Chanel.

Chanel had that kind of beauty that makes you sit up a little straighter. Angelic smile, soft features, and the kind of presence that makes you feel like you need to come correct—or not come at all. I hit that “Add Friend” button like I was on Family Feud with one hand already on the buzzer.

We started talking. At first, it was every other day. Then every day. Conversations about school, passions, goals—all the good, building-block stuff. She was into fashion and modeling. I was deep into photography. We made sense. I was country; she was city. She taught me things—how to move, how to navigate, even how to ride public transit, step by step, through text like a GPS with personality.

But here’s where the plot thickens.

Weeks after I moved to Atlanta and started school, we still hadn’t met in person. I wanted to—but I was also… stalling. Equal parts excited and hesitant. Eventually, we made it happen.

We met at the main entrance of the school.

And just like that… I forgot how to be a human being.

Texting me? Oh, I was smooth. Conversational. Probably a little funny. But face-to-face? I turned into a statue with a pulse. I don’t think I’ve ever been that quiet in my life. If there had been a fire alarm nearby, I might’ve pulled it just to create an exit strategy. I was starstruck, plain and simple. Here I was, standing in front of a woman I thought was way out of my league—and somehow, she liked me.

We stood there for about ten minutes and barely exchanged ten words. A statistical disaster.

A few days later, Chanel let me know how she felt about that encounter. I don’t remember every word, but I do remember one landing clearly: uncomfortable. And honestly? She wasn’t wrong.

At 20, I was still figuring it out—confidence, communication, self-belief. My shyness had me procrastinating in real time. My lack of confidence had me second-guessing moments that didn’t need interrogation. I was present physically, but mentally? Still buffering.

But growth has a way of pulling up on you, whether you’re ready or not. As I got older, I started to understand myself better. I got more comfortable in my own skin, more confident in my voice, and more willing to step forward without overthinking every step. Eventually, I reached a point where I believed—not arrogantly, but honestly—that I could walk into a room and connect with anyone in it.

And if Ari Lennox taught me anything, it’s this: sometimes the moment doesn’t need perfect timing—just a little courage and the willingness to say what you actually feel.

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