I wake up to the smell of coffee brewing from my pre-set pot like it’s a supporting character in my morning routine sitcom. Sure, I could get one of those sleek pour-over contraptions, but this old drip machine has personality—kind of like me before I’ve had my first cup. The mornings in my South Side Chicago apartment are my quiet time, a rare moment of stillness in a city that feels like it’s always grooving to the rhythm of a hidden bebop track.
Morning Rituals: Jazz, Journals, and a Side of Self-Discovery
My mornings are sacred because they set the tone for the day—and honestly, they keep me centered in a world that sometimes feels like a dating show where the contestants keep forgetting the rules. Take dating, for example: You’d think pouring your heart into connections would come easily for someone like me, a writer who dissects every interaction like Kanye samples soul tracks. But here’s the thing—they don’t exactly teach “navigating relationships” in African American Studies courses.
Every morning, I spend about 15 minutes journaling. It’s not deep, “dear diary” stuff—I mostly jot down dreams, random ideas for short stories, or reflections on yesterday’s conversations. It’s amazing how often my dating life sneaks into those pages. One time, I spent three paragraphs wondering if a woman’s choice to order pineapple on her pizza during our first date was a red flag or just quirky charm. Spoiler: It was quirky charm. (We had a good run before parting ways—amicably, of course.)
Afternoon Hustle: Work, Walks, and Nuanced Observations
By the time I’ve warmed up to the day—and sufficiently caffeinated—I dive into my work. That could mean hammering out pages for my latest project or, on tougher days, staring at a blinking cursor while whispering, “Please, God, just one more sentence.” As a writer, storytelling is all about layered truths, whether I’m capturing Chicago’s gentrification saga or the delicate dance of modern romance.
Around noon, I step out for a game I like to call "Walking Chicago Bingo." South Loop hipsters? Check. Neighborhood auntie yelling at someone about dirty Tupperware? Double check. It’s during these walks that I do some of my best thinking. I’ve even worked out personal relationship faux pas on these strolls. Case in point: One spring afternoon, listening to old-school Common on my headphones, I realized I’d been ghosting someone—not intentionally, but my "Sorry, I’ve been busy" vibe wasn’t it. That revelation led to an overdue apology, and while it didn’t rekindle our spark, it taught me to be real about where I stood with folks.
Unexpected Lessons from the Everyday
If there’s one thing Chicago has taught me, it’s that life (and love) is all about the small moments. Take my gas station debacle last winter. I’d stopped for a fill-up on a frozen January night when a dude struck up a conversation—normal Windy City camaraderie. Midway through, he told me my windshield was as dirty as his last relationship. Savage? Absolutely. But his quip got me thinking: When it comes to relationships, sometimes we ignore the dirt until someone says, “Hey, time for a clean-up.”
Cue self-reflection: What red flags had I ignored in past relationships? Is there clarity that needs to come before I hit the road again, metaphorically speaking? (Also, I cleaned my windshield. Shout-out to that random guy for the life advice.)
Evening Rhythms: Intentional Connections and Late-Night Thought Spirals
Evenings are for connection. Whether it’s catching up with my parents—my mom asking if I’m eating enough vegetables is her love language—or vibing out to Miles Davis’ Kind of Blue while texting friends, this is my soft space. I also lean into face-to-face time when I can: dinner with close friends or a spontaneous "let’s grab cocktails" moment with someone new.
Let me say this: Dating in your 30s hits differently. It’s less, “Who’s right for me right now?” and more, “Can this person groove with the lyrics of my life?” After a certain point, surface connections don’t do it for me anymore. I’ve learned to ask myself: Do we vibe beyond the top-level stuff? Could they sit through one of my stream-of-consciousness jazz rants—because those happen—or talk about Gwendolyn Brooks over brunch?
On a great date night, there’s laughter, shared fries, and maybe an inside joke about whether peanut butter belongs on burgers (it does not, for the record). On an iffy date night, I’ll catch myself people-watching and wondering whether these two folks at the next table are destined for forever or an awkward ghosting situation by Friday.
Closing Time: Keeping It Grounded
As the city lights twinkle and train horns hum in the distance, I wind down back at my apartment with a glass of wine or, on busier weeks, my third bottle of sparkling water (yes, I’m that guy). And then, the night ends where the day began—in reflection.
Some nights, I laugh at how romance gets tangled up in everyday life—like when I spilled coffee on my shirt before a virtual date or confused someone’s love of EDM with an actual shared interest. Other nights, I sit silently, grateful for the lessons hidden in messy first dates and deep second chances.
Every day isn’t perfect, but it’s mine. And whether I’m navigating my next creative project or figuring out how to be a better partner, I remind myself that this journey—messy, beautiful, and unpredictable—is worth it. After all, like the jazz that breathes through Chicago’s alleys, life doesn’t follow a strict script. It improvises.
So here’s the takeaway: Lean into the small, unexpected moments. Relationships—whether they’re with others or yourself—are designed to catch us off guard. And that’s where the magic is.
