I don’t think you really leave the South Side of Chicago; it’s stitched into you like the lining of an old coat, familiar and dependable no matter how far you go. For me, it’s the soundtrack of wind rustling through el tracks, the rhythm of sneakers slapping concrete, and the scent of Harold’s Chicken lingering in the air like a benediction. Chicago can harden you, sure. But it also wraps around you, soft as summertime jazz drifting from a neighborhood block party. This is the place that made me—and it’s taught me more about relationships than any self-help book stacked up at the front of Barnes & Noble. You see, love—just like Chicago—can be gritty, unpredictable, full of potholes, but always worth the ride.

The Heartbeat of a Neighborhood: Where Love Learns to Hustle

Growing up on the South Side, I learned early that everything good takes work. You don’t find fully bloomed roses in the cracks of the sidewalk—you plant them and pray for rain. My parents’ marriage wasn’t a Hollywood story with tear-soaked declarations and violins swelling in the background. Nope. Their love was a jigsaw puzzle pieced together over Friday-night arguments about the grocery bills and reconciliations set to episodes of Wheel of Fortune. They were each other’s backbone, even when life bent them forward—a quiet kind of love, built to last.

That’s the first lesson Chicago taught me about relationships: Build love slow, like a good jazz riff. The kind that sneaks up on you, syncopated and soulful, rooted in trust and everyday investment. Flashy isn’t the goal. Just like a hot summer fling can’t replace the warmth of the furnace in February, infatuation alone won’t keep you together when life hits like a January wind off the lake.

Connections as Strong as Maxwell Street Polish

There’s nothing like fighting to save a neighborhood to remind you what real community—and by extension, real love—looks like. When I was seventeen, my block became the front lines in Chicago’s gentrification war. Developers started cutting down familiar storefronts like they were slicing through history. And yet, my neighbors didn’t take it lying down. The auntie selling catfish sandwiches at the corner hub, the old men playing dominoes outside the barber shop—they all pushed back, dug in, and stood tall.

That’s the second lesson Chicago hands you about relationships: Love is a verb, not a noun. It’s showing up, giving up your weekends, speaking up even when it feels inconvenient. Love might start with a spark, but survival depends on the fuel you throw on the fire. Whether it’s romantic or platonic, the kind of bond that endures isn’t passive. It grows because you both make room in your lives for each other—like how the corner convenience store guy always knew to toss me an extra pack of Now and Laters during my broke college days. Because that’s what love does. It feeds you when you don’t even know how to ask.

Dating Lessons from the Green Line

If you’ve ever taken the Green Line train during rush hour, then congrats—you’ve survived the ultimate metaphor for modern love. Clutching a pole with one hand and your nerves with the other, you’re acutely aware of everyone else’s energy. Chicago trains vibe like their own reality show: combative uncles, young lovers whispering secrets, solo riders lost in the low hum of their headphones. It’s chaotic but utterly captivating.

Early in my dating life, I learned that love works similarly. You don’t get to control the ride entirely—but you do get to choose how you respond. Will you doggedly hang on somewhere in the ride’s chaos, or bail at the first station when things get real? The Green Line reminds you that love requires flexibility. You’re stuck in close proximity to someone else’s mess—literal and figurative—and part of the journey is deciding what you’re willing to share and absorb.

But the train also reminds you of the possibilities. Every now and then, there’s a spark: a chance smile between strangers or an unexpected seat opening right when you thought your legs were going to give out. Just like love, public transportation surprises you when you least expect it. Sometimes, it’s messy; sometimes, it’s magic.

Lake Michigan—and the Backdrop of Forgiveness

I had my first real heartbreak while staring at Lake Michigan. It was one of those quintessential young relationships—heavy on passion, light on reality checks. The kind of love where every fight feels like a natural disaster and every kiss like the end credits of a John Hughes movie. When we broke up, I found myself walking aimlessly along the shoreline, past Navy Pier and toward Promontory Point, where waves slapped against the rocks. It was January, bitter cold, and I didn’t have gloves. Rookie mistake.

You see, I thought the lake would give me answers, but all it gave me was time—time to notice that even water has a way of softening jagged edges over time. And this taught me the next lesson about love: You can’t skip forgiveness, whether it’s for someone else or yourself. Every relationship will drop you off at its version of Lake Michigan—a place where you either drown in resentment or let go and float. Chicago’s landscapes taught me that catharsis doesn’t come easy, but it comes eventually, in ripples rather than waves.

The City That Holds You to Itself

Even on days when Chicago feels unforgiving—when the sky is steel-gray and commuters are walking so fast they blur—I still feel its pull. When I step off the Red Line and hear a street performer riff on a Marvin Gaye track, or when I grab a perfectly greasy Italian beef from Al’s, the hold tightens. This city isn’t perfect, and it never pretends to be. It’s loud, opinionated, sometimes a bit of a mess—and yet, it always manages to offer a kind of healing that other places never could.

Love operates the same way. It’s not just about passion or perfection; it’s about the moments that stitch themselves into your being, shaping you in ways grand and subtle. The right kind of love—like the right kind of city—becomes your anchor, no matter where you roam.

You don’t have to be from Chicago to learn from it, though. Wherever your “place that made you” is, take the lessons it offered. Learn to hustle for what matters, whether it’s that fresh connection you’re building or the long-term love you’re nourishing. Show up, forgive often (but not too quickly), and leave space for the messy, unplanned magic.

Because here’s the thing, from this Chicagoan’s perspective: Building love and navigating relationships, much like living in a city, demands resilience, optimism, and paying attention to what makes your world hum. And when that world comes alive—when you find your version of summer on the South Side—you’ll know you’re in the right place, with the right people.