It’s 6:43 p.m. on a Friday, and I’m standing in line at Harold’s Chicken on 87th Street, waiting for my order: a six-piece, mild sauce, no coleslaw, extra fries. The air smells exactly as you’d expect—fried, salty, slightly sweet with the tang of hot sauce dancing somewhere at the edges. The line winds almost out the door, people debating everything from Bulls trades to whose grandma still makes the best peach cobbler. To me, this place is more than just food. It’s a microcosm of South Side Chicago life. It’s home—the noisy, unapologetic, don’t-you-dare-ask-for-ketchup kind of home.
Somewhere between the shout for "next order!" and the buzz of someone’s phone blasting Chief Keef, I realize just how much this city raised me, taught me, and stayed with me. And somewhere in those lessons—between block parties and CTA buses always being late—are truths about love, identity, and relationships that run just as deep as any jazz riff spilling out of an open window on King Drive. So, let me take you on a tour of the city that made me who I am, with a few life lessons from my Chicago upbringing thrown in for good measure. Spoiler alert: You don’t have to be from the South Side to relate, but it helps if you know your way around a barbecue grill.
The Church Basement Taught Me About Leave-and-Cleaving (Yes, That’s a Thing)
Every Sunday, my family would pile into our faded green minivan and make our way to church. If there’s one thing South Side churches know how to do, it’s turn even the smallest event into a community affair. Baby shower? Church potluck. Auntie got a new wig? Church potluck. Miss Mabel’s dog survived surgery? You guessed it—church potluck.
In that cramped basement, I learned everything from the delicate art of balancing macaroni-and-cheese on a flimsy paper plate to the dynamics of romantic relationships. There was always a newly engaged couple being paraded around, usually holding hands so tightly you’d think they were glued at the palms. I remember overhearing one of the older deacons say, “Leave and cleave, boy. That’s how you build something real.”
As a kid, I didn’t understand what the heck he was talking about. Now I do. Love, in any lasting form, is about identifying what’s worth holding onto and what’s worth letting go of. It’s knowing when to leave the noise behind—whether it’s self-doubt, unresolved baggage, or even well-meaning but overbearing family members—and cleaving to what matters. Spoiler: If Harold’s chicken wings are invited to the wedding and I’m not, I’m rethinking the whole thing.
The Block Party Rules: Be Seen, Be Cool, Be Authentic
Summertime in Chicago brings out two things: rooftop cookouts and block parties. Our block hosted one every July. Someone always brought out the big stereo system blasting Frankie Beverly and Maze, while kids sprinted through open fire hydrants like they were auditioning for a Nike commercial. Meanwhile, the older folks grabbed folding chairs and yelled out unsolicited dating advice from the sidelines. “You need a woman who can fry some fish!" “Don’t trust a man who irons his jeans!”
Block parties were perfect practice for relationships because they demanded one thing: authenticity. When you’re surrounded by people who’ve known you since you were trying to stomp the yard at middle school talent shows, there’s no hiding behind a mask. You learn quickly that the most attractive thing isn’t what you’re wearing, but how comfortable you are with yourself.
In dating, people can sense when you’re trying to be someone you’re not. It’s like pulling up to a barbecue claiming you made the potato salad when everyone knows you can’t boil water. The same way you walk into a block party rocking your authentic self, you should walk into your relationships with confidence in who you are. Because trust me, it’s exhausting trying to be anyone else—and the kids running through sprinklers don’t care either way.
The Green Line Taught Me You Can’t Always Control the Journey
Riding the CTA’s Green Line from Ashland to the Loop is an exercise in patience and trust—two things every relationship needs in spades. Some days the train comes on time, the doors swoosh shut, and you’re treated to a relatively smooth ride into downtown. Other days? It’s delay after delay, punctuated by “sick passenger” announcements, the occasional argument breaking out in the adjacent seat, and someone yelling “This my album—stream it on SoundCloud!” over muffled beats.
The Green Line, much like love, rarely goes exactly as planned. There will always be wrong stops, unscheduled pauses, and detours that force you to sit with the unexpected. It’s frustrating, humbling, and kind of beautiful if you let it be.
I had a relationship once where I kept trying to control every little element—when we’d text, what our dates looked like, even how fast we were “supposed” to fall in love. I thought I could plot the journey down to the last detail. Spoiler alert: it didn’t work. Love, like Chicago transit, doesn’t care about your plans. The only thing you can do is stay the course, embrace the pauses, and enjoy the ride when it’s good. Oh, and avoid sitting too close to the train car doors when it's rush hour—trust me on that one.
Harold’s Taught Me the Value of Sweet with the Spicy
As my order finally gets called, I sit down with my steaming six-piece and immediately reach for the mild sauce—Chicago’s Mona Lisa of condiments. Tangy, slightly sticky, with just enough sweetness to balance the heat of the fried chicken. Mild sauce is the culinary equivalent of “soft on the outside, fire on the inside,” and if that doesn’t describe a great relationship, I’m not sure what does.
Love demands that same balance of sweet and spicy. It’s about those tender moments—holding hands during long walks, sharing inside jokes at 2 a.m., or sneaking glances across the room—and also the fiery ones, where passion and conviction collide. That balance is what makes connections memorable and, more importantly, worth savoring.
So, when mild sauce dribbles down my fingers, I’m reminded: never settle for anything too mild or too hot in love. Look for that sweet spot, the one that makes you tingle a little, laugh a lot, and maybe—even if just for a moment—forget the world beyond the diner booth.
Conclusion: Where You’re From Is Who You Are—and That’s Enough
Chicago raised me, shaped me, and handed me more life lessons than I ever asked for. From the gospel echoes of church basements to the loud Uncle Larry wisdom of block parties, from the relentless hum of the Green Line to the magic of mild sauce, this city taught me what it means to love deeply, walk authentically, and stay present through life’s inevitable delays.
Wherever you’re from—whether it’s a big city, a sleepy suburb, or anywhere in between—there are lessons hiding in the stories of your hometown. Embrace them. Take them into your relationships, your dreams, and your Saturday night Harold’s runs. And most importantly, wherever life takes you next, know this: home isn’t just the place that shaped you. It’s the love you carry with you into every connection you make.
