The Weirdest Thing I’ve Ever Done for a Story

I still remember the moment my editor called me with the pitch. “What if,” she said with barely disguised glee, “you become a professional matchmaker for a month? You know, undercover. Write about the whole experience.”

“Undercover,” she said. As though I would be donning a trench coat and sunglasses in some sort of romantic espionage film. But here’s the thing: I don’t know how to say no to a challenge. And so, I—someone who can start a heated debate at a dinner party over whether Jane Austen was sneakily funny or just polite—jumped straight into the matchmaking world armed with nothing more than a day planner, my ability to read people, and the Google search history of a woman desperate to sound competent on her first day.

Here’s how it went. Spoiler alert: let's call it a chaotic mix of rom-com blunders, heartwarming moments, and the occasional existential breakdown.

Crash Course in Cupid-ing

First things first, I needed to learn what matchmakers actually do. Turns out, it’s not as glamorous as those TV shows where professionals set up suave city dwellers over candlelit dinners. Real matchmaking involves spreadsheets. Lots of spreadsheets. I spent my first few days inputting client profiles into a vast database: allergies, hobbies, ideal first-date locations—a mix of the mundane and the oddly specific (one man listed "must love dodgeball" as a deal-breaker).

The pressure was real. Every bio I read felt like flipping through some modern art exhibit titled Human Longing in the 21st Century. There were hopeful phrases (“looking for my partner-in-crime”) and brutally candid ones (“divorced, distrustful, but willing to try”). Everyone was vulnerable in their own strange way, and my job was to find them someone to share that vulnerability with. No big deal, right? Just the literal hopes and dreams of strangers sitting in my hands, next to my lukewarm cappuccino.

A Meet-Cute Gone Wrong

My role wasn’t just databasing; I also shadowed during some actual first dates. This was supposed to help me “understand the chemistry,” but in reality, it felt like being a referee for some bizarre, high-stakes game of Ping-Pong.

Take one match I observed at a vegan café. Let’s call the daters Mari and Keisuke. Mari showed up in a flurry of silk scarves and positivity, the type of person who nods appreciatively when you pronounce quinoa correctly. Keisuke, on the other hand, exuded the moody charisma of a Haruki Murakami protagonist—brooding but likable.

It should’ve been perfect, except Mari started grilling Keisuke on whether he grew his own kale (he did not), and Keisuke retaliated by quoting Nietzsche out of context ("Marriage is the death of passion"). Ten minutes in, Mari excused herself to the bathroom and, I kid you not, texted me: “Can we get a life coach to fix him?”

At that moment, I realized matchmaking is 60% intuition, 30% patience, and 10% reminding people that they cannot change their date into a Pinterest board version of themselves. I made a mental note to start carrying emergency chocolate for future dates.

Playing Love Doctor

Midway through my month-long stint, I attempted to provide advice to clients directly—a task I was wildly unqualified for and, unfortunately, enthusiastic about. This led to a moment I now describe as “The Great Love Resume Catastrophe.”

One client, Yukiko, wanted me to help her “rebrand” her personality for potential matches. She said, “Think of me as an old company going public. I need a logo, a tagline. Something that screams successful yet humble.” But what Yukiko really wanted, of course, was to feel understood and desirable—a universal craving disguised in corporate lingo. I approached this like the former museum curator I am: methodically and with too much zeal. I suggested she frame her personality in terms of eras.

“You’re vibrant, like the Impressionists!” I exclaimed. “Bold, yet approachable. With just enough mystery to keep people curious.” Yukiko squinted at me as though I’d just handed her a particularly cryptic crossword clue. The conversation derailed when she Googled “what is Impressionism” on her phone in real-time and decided it made her sound “stuffy.” I’ll just say this: branding your love life as an art movement is not for the faint of heart.

Bridging the Awkward Gap

What I learned by the end of this odd, hilarious project is that everyone—whether they’re swiping on apps, hiring a matchmaker, or whispering "marriage is the death of passion”—is just trying to connect. Along the way, we get hung up on details: kale farms, Instagram aesthetics, résumés that sound like they belong on LinkedIn.

But connection rarely grows out of perfectly scripted moments. It grows in all the awkward ones. Like when a match doesn’t know what to say and overorders on dessert to stall. Or when, after a disastrous first date, someone sends a surprisingly sweet follow-up text that says, “Sorry I was weird. Can we try again?”

All those clumsy moments are what form the basis of real relationships, not curated perfection.

Lessons from a Reluctant Matchmaker

Though my career in matchmaking was short-lived (and inspired far more chaos than Cupid), here are a few things I wish I could bottle up and give to anyone still searching for their person:

  • Let Vibrancy Trump Perfection: Forget the “perfect” bio—or person. It’s your quirks, your slightly messy vibrancy, that make you memorable. Lean into them.

  • Don't Kill the Text Game: Forget grand overtures for a sec. Sometimes, sending that little “Hey, how’s your day?” can be braver and more impactful than any poetic declaration.

  • Flaws Are Unavoidable: Everyone comes with flaws, quirks, or at least an aversion to your favorite vegetable. The magic is finding someone whose weirdness meshes with yours.

From Chaos to Clarity

By the end of my matchmaking escapade, I felt simultaneously exhausted and deeply grateful. No, I didn’t suddenly unlock the secrets of love—or turn into some clairvoyant relationship guru—but I did learn this: love is equal parts science and mystery.

So if you’re worried about your quirks, your marinated-egg obsession, or the fact you’ve never once replied to a text in under 24 hours—don’t stress. You’re exactly weird enough to find someone, trust me. Even Nietzsche probably had a soulmate. Or at least, someone who tolerated him quoting himself on first dates.