You never forget your first.

For some, that phrase might conjure memories of a first kiss, that awkward high school slow dance, or even a make-or-break moment on a first date. For me? It’s the day my first byline was published, cementing my transition from daydreaming wordsmith to a fully-fledged writer. It wasn’t just a step in my career—it was like that first swipe right that turned into an actual conversation. One moment you’re out there, hoping your words connect, and then suddenly, they do.

Let me take you back.

The Setup: A Coffee Shop, Three Rewrites, and Zero Chill

I was fresh out of college and splitting my time between running creative writing workshops for local teens and barely-affording-my-rent freelance gigs. Picture this: I was hunched over my laptop in a Hyde Park coffee shop with a caffeine buzz strong enough to make my hands shake. The editor of a now-defunct Chicago lifestyle website had asked me to submit a piece on “The State of Dating in the City.” The deadline was tight, and the stakes felt Olympic-level.

At the time, South Side dating wasn’t just about finding the right person; it was about dodging dating faux pas while balancing dreams, ambition, and your CTA card budget. A bad date might mean you’re stuck with someone who didn’t respect your grind—or worse, didn’t know Harold’s Sauce Rule #1 (mild or hot, but BBQ sauce only if you’re brave). It was this absurd, messy magic I wanted to capture. After a few false starts and at least three too many references to Chicago hot dogs (a writer learns, okay?), I submitted the piece. Then I spent the next week holding my breath like I was waiting for the smoke detector to beep.

That First “Yes”—And a Little Jazz Hands

When the acceptance email came through, I danced. And not the cool kind of dance you might imagine Miles Davis might have played in the background of—this was jazz-hands-meets-salsa hysteria. My parents were proud, my best friend immediately teased me, and my cousins from across the city passed around the link like it was a mixtape.

Still, I was hit with my first (and every writer’s perpetual) fear: what if people hated it? Worse, what if no one read it? That “yes” was thrilling, but then came the real kicker—was I good enough to reach someone, anyone, with these words?

Spoiler alert: people did read it. And the feedback? As mixed as a late-night playlist. Some folks loved my take on why Chicago’s weather makes cuffing season so complicated, while others emailed in to vehemently disagree about pizza being a dealbreaker topic. One commenter passionately debated my stance on public transit flirting—and honestly, they had a point. Flirting on the Red Line? Risky business.

What I Learned: Almost Everything Is Like Flirting

As it turns out, putting your words out into the world isn’t all that different from putting your heart out there in dating. (Yeah, here comes the metaphor. Buckle up.) Your first article, like that first crush or first online dating message, feels like the absolute biggest, most defining thing. You polish your jokes, overthink whether the tone hits right, maybe beat yourself up over a typo. But once it’s out there? You let go and hope it connects.

Here are a few lessons I carried from that day—and honestly, they work for dating just as well as they do for publishing:

  1. Be clear about what you want and who you are. You have to stand for something in your work, whether that's a unique perspective or a shameless ode to deep-dish pizza (no judgment here). Same goes for dating: if you’re all about local jazz nights and taco spots, own it. Authenticity rings louder than perfection.

  2. Rejection is not personal. Not everyone’s going to vibe with your story. Or your jokes. Or your unapologetic love for Wicker Park on Tuesdays when it’s not too crowded. That’s okay. For every miss, there’s someone who gets it—and gets you.

  3. It’s okay to be vulnerable. My first byline worked because I wasn’t afraid to get real. I wrote about the hilarity of asking your crush to meet you halfway across the Green Line or how dates sometimes feel like job interviews with better lighting. Digging into those truths—funny, awkward, or tender—not only made my story relatable, but it helped me find my voice.

  4. Sometimes, just showing up is the win. Clicking “submit” was a victory on its own. Same in the world of love—sometimes just saying yes to the date or putting yourself out there is enough to celebrate.

The Ripple Effect

That first article wasn’t winning any Pulitzers, but it got people talking. It got people thinking. And honestly, most importantly, it got me thinking. For the first time, I saw what it felt like to plant a tiny idea in someone else’s world and let it grow. For all the uncertainty in writing (and dating), that connection—that pause-while-reading moment—remains magical.

To this day, I carry the thrill of that first byline. It’s a reminder that even the smallest start can grow into something life-defining. Like that first coffee date with someone who later became your late-night philosophical debate partner, or the first text that turned into a years-long inside joke.

Your First Time, Too

If you’re reading this, wondering when to take the leap—on a date, a project, or whatever dream lights your fire—consider this your sign. You don’t have to have it all perfect. I made typos in that first article (and at least three since writing this sentence). You don’t have to feel 100% ready, because who ever does? The point is to start.

And if you fall flat the first time, know this: even stumbling forward is better than standing still. Whether it’s your first published piece, first declaration of love, or first attempt at deep-dish pizza, the joy is in showing up and daring—jazz hands and all.