Introduction: The Complicated Romance with Home

Growing up on the South Side of Chicago was like being in a relationship with someone who knew exactly how to light up your world one moment—and test every ounce of your patience the next. On one hand, there’s the undeniable beauty: the rich history, the unapologetic energy, and that sense of community that shows up when it counts. On the other? Let’s just say potholes, abandoned storefronts, and a winter wind so ruthless it makes you question every choice in your life don’t exactly scream “unconditional love.”

Chicago has always been “ride or die” in my story. It’s stubborn and raw, with a flair for jazz and a determination that mirrors mine. But like any long-term commitment, my relationship with home is complex, messy, and sometimes full-blown toxic. And yet, just like with a childhood sweetheart, I keep coming back. Here are the highs and lows of my love/hate relationship with where I grew up—and why it still feels like home.

The Sweet Spot: Where Roots Go Deep

I’ll admit, there’s a magnetic pull to the South Side that no other place can replicate. It’s in the rhythm of the elevated trains squealing overhead, the impromptu block parties that remind you music can heal anything, and the way the sunsets over Lake Michigan feel like a painting someone forgot to frame. It’s also in the way churches open not just their doors, but their hearts.

Growing up in a community like mine, you learn early on that family isn’t just about DNA. The neighbor who babysits you while your mom teaches Shakespeare? Family. The barber who debates Bulls trades with your dad like it’s his civic duty? Family. And the woman on the block who gives shady side-eyes to the new guy driving too slow in his car? Family, too—if only for her unshakable dedication to neighborhood security.

These layers of familiarity and loyalty wrapped me up like a well-worn quilt. I learned resilience from everyday faces, strength from hard conversations, and pride from stories of how our streets birthed greatness: Gwendolyn Brooks writing about Bronzeville, Sam Cooke blessing us with that voice, and Chance the Rapper shouting out Harold’s Chicken like it’s gospel. Being from here isn’t just about geography; it’s a statement: “I survived. I thrived. I’m South Side born and raised.”

The Heartache: When Home Lets You Down

But let’s get real—love, even for your hometown, isn’t all warm hugs and church tambourines. Being from here also taught me what it feels like to question whether you’re wanted in your own neighborhood. Because sometimes, home doesn’t feel like it loves you back. There’s a special hurt that comes from watching your neighborhood stores boarded up, your friends moving out, and the news treating your zip code as some post-apocalyptic subplot.

Then there’s gentrification, the kind of sneaky ex that keeps showing up at all the wrong times. Once, I walked into this trendy coffee shop that popped up exactly where Ms. Hattie’s soul food spot once stood. Let me tell you: the walls might’ve been painted white, but I still smelled fried catfish in the air, and no amount of overpriced lattes could erase that.

The South Side is full of contrasts like this. You’ll walk past brilliant murals celebrating Black joy on one block—and a playground with broken swings on the next. It’s like being in a situationship where one minute, you’re swooning, and the next, you’re wondering why you even stayed. But no matter how familiar the heartbreak, it still stings every time.

Lessons in Love: Taking the Good with the Bad

If there’s one thing living here has taught me, it’s that loving something—or someone—means loving all of it, not just the Instagram-filtered parts. I used to hate how my dad would grumble about car repairs after hitting those South Side potholes (seriously, why hasn’t NASA been contracted to fix these things?). But now? I laugh about it like it’s some twisted badge of honor. Those potholes are part of the package, just like the sound of ice cream trucks in July or the uncle at every barbecue who insists an $8 grill from Jewel can feed 20 people.

When we talk about relationships—whether with people, places, or even ourselves—we tend to expect perfection. But home, flawed as it is, has a way of teaching you how to build something meaningful out of all the cracks and chaos. It’s taught me to embrace duality: I can love my city deeply and critique it just as fiercely. Sometimes, that’s the healthiest kind of love there is.

What “Home” Teaches Us About Relationships

Here’s the thing: cities are like the people we date. You wouldn’t dump someone over one bad argument (or one hellish Chicago winter). You weigh the good against the bad. Home, for all its complications, has shaped me in ways I could never duplicate elsewhere—and truthfully, isn’t that what we’re all looking for? A connection so real, it molds us?

In love and in hometowns, we crave belonging. That childhood nostalgia? That creativity born of struggle? That deep satisfaction of knowing every crack in the sidewalk and every melody in the summer breeze? That’s home.

Loving Chicago has taught me to honor complexity—not just here, but in how I connect with others. Just like my city, people have layers of beauty and brokenness. There’s value in sticking around when things aren’t easy and celebrating the quirks that make someone—or someplace—uniquely theirs.

The Takeaway: Carrying Home Wherever You Go

I’ve flirted with other cities, sure. Paris had its dreamy terraces and its soft-lit romance; New York had its electric energy and bagels. But no matter where I’ve gone or who I’ve tried to be, I’ve always found myself yearning for the unapologetic rhythm of a place that embraces me for who I am: South Side, through and through.

Here’s my advice, whether you’re wrestling with complicated feelings about your hometown or figuring out if your partner’s quirks are deal-breakers or deal-tolerables: Ask yourself what lasting lessons that person—or that place—has gifted you. Have they pushed you to grow? Fed your soul in ways you’ll never forget? Made you laugh when you most needed it? If the answer is yes—even layered under frustrations and flaws—maybe it’s worth sticking around.

Home isn’t always a fairytale, but it’s in the imperfections where the real story lies. For me and my city, it’s a long story—messy, beautiful, frustrating, and still unfolding. And to borrow some wisdom from a South Side icon, Mr. Common himself: “Home is wherever we can make it.” But Chicago? Chicago will always be where my heart beats loudest.