If you’ve ever wondered how far a writer will go to get a story, let me assure you—it’s further than most rational humans would. Case in point: the time I braved wind, snow, and unrelenting awkwardness to crash an underground speed-dating event at a Chicago laundromat. Yes, you read that right. A laundromat.

This little escapade started as a throwaway idea in an editorial meeting. “Wouldn’t it be wild,” someone said, “if we explored unconventional places people find love?” Next thing I know, I’m nodding along like I don’t have a million better things to do on a Thursday night than accidentally bleach my black hoodie while pretending to be single for "the sake of journalism."

But hey, sometimes the most bizarre assignments are also the ones that teach you the most—including unexpected lessons about relationships, humanity, and the delicate art of interpreting spin-cycle flirtation.

Chapter One: Spinning Hearts and Slippery Socks

The venue alone was a dare. Picture a small laundromat, just off 63rd, the kind of place where the machines rumble so loud that even shouting sounds quaint. Someone had shoved the industrial dryers aside to make room for a folding table, a cheap speaker, and a handwritten sign that read, “Loads of Love: Speed Dating Night.”

The organizer, a wiry man in a bowler hat who went by “Smooth Tony,” greeted me like this was Studio 54. “You’re gonna love it here,” he said, practically vibrating with enthusiasm. “Laundry brings people together in ways the apps can’t.” I wanted to tell him he was overselling it, but his grin was infectious—or maybe I was just too curious to bolt.

Now, I wasn’t entirely lying when I said I was “single” that night, but I also wasn’t entirely truthful. I had been seeing someone—let’s call her Maya, a lawyer with a fierce wit and an even fiercer collection of combat boots. This wasn’t a titleless relationship so much as a “we’re taking it slow” situation. Suffice it to say, this assignment was walking a real fine line.

My plan was simple: Blend into the crowd, observe quietly, and maybe throw a curveball question or two at the participants. What I didn’t plan for was Smooth Tony cornering me and throwing my name on a clipboard. “You’re up third,” he whispered, giving me a wink like we were old war buddies. Before I could protest, I was being shoved toward a folding chair, the kind your aunt brings to Fourth of July picnics.

And so began the weirdest—and most Chaotic Neutral—13 minutes of my life.

Chapter Two: Small Talk in Close Quarters

It started innocently enough. My first partner, a woman wearing a Tupac hoodie, told me her favorite food was “gas station taquitos—don’t judge.” Immediately, I knew she was someone I wanted as a character study. My second partner, a guy named Larry, brought a notebook full of hypothetical questions like, “If your soulmate was in one washing machine and a winning lottery ticket was in the other, which would you save?” I told him I’d grab the ticket and use the winnings to hire a search-and-rescue team. He called me a capitalist, I called him delightfully exhausting, and just like that, our three minutes were up.

By round four, I lost any hope of remaining inconspicuous. A woman wearing a glittery beret eyed me suspiciously the moment we sat down. “You’re not really here for love, are you?” she asked, her voice cutting through the cardio soundtrack that Smooth Tony had somehow deemed romantic background music (yes, think “Eye of the Tiger” but for your feelings). I stammered out something about “being open to new experiences,” but she wasn’t buying it.

“You’re a spy,” she whispered dramatically. “Or worse. You’re a writer.”

Busted. I gave her a sheepish smile, and to my surprise, she smirked back. For the rest of our three minutes, we swapped impressions of the laundromat dating ecosystem like we were judges on a reality TV show. Her verdict: “Love in the time of fabric softener is either the greatest rom-com or the saddest Black Mirror episode of all time.”

Chapter Three: The Question No One Asks

You’d think this would be the part where I quietly slipped out the side door, but then someone hit me with a question I wasn’t prepared for: “What’s the weirdest assumption people make about love?”

It was round seven—participant number whatever—and a guy in a varsity jacket was flashing me a grin that was somewhere between cocky and curious. Maybe it was the adrenaline of the night, or maybe I was just too weary to deflect, but I forgot I was supposed to be undercover. I answered honestly.

“We expect it to be effortless,” I said. “Like, if it's meant to work, it just works. But a good relationship is like a jazz piece—it sounds improvised, but there’s so much care and intention behind it. You can’t fake that harmony.”

It sounded a lot deeper than I meant it to, and—for once—varsity jacket guy didn’t seem to have a follow-up. He just nodded slowly and said, “Damn, man. Truth.”

For a moment, it didn’t feel like an article assignment or an undercover date. It felt like a real conversation—two strangers leveling with each other over the din of tumbling socks.

Chapter Four: Lessons from the Spin Cycle

When the night concluded, someone handed out fruit snacks as a “thank you for coming” gift. I tore into mine as I sat by the window, watching couples linger over stray socks and forgotten sweaters.

I didn’t find a groundbreaking exposé that night, but what I did find was this: Dating—whether it’s under flickering fluorescent lights or in the moody glow of a rooftop bar—is about showing up, being awkward, and occasionally surprising yourself. It’s messy, unpolished, and sprinkled with moments of hilarity—and isn’t that what makes it kind of beautiful?

For all its quirks and absurdities, that laundromat reminded me of something simple yet profound: Love thrives when you meet people where they are. Whether that's standing in front of a washing machine or sipping overpriced lattes, what actually matters is the bravery of putting yourself out there, no matter how ridiculous it feels.

The Spin Cycle Takeaway

Relationships, much like laundry, require effort. You can’t let things pile up for too long, and sometimes a little detergent (aka vulnerability) goes a long way. And perhaps most importantly? Sometimes you find yourself having the most fun in places you’d never expect—as long as you’re willing to lean in, rinse thoroughly, and repeat.

So the next time a quirky opportunity comes your way, take it. Say “yes” to the weird date, the unfamiliar space, or, you know, a speed-dating night at your local laundromat. Worst case scenario? You leave with a clean pile of clothes and a story to tell.

And best case? You might just find yourself loading your whites and your colors into the same washing machine for two.