The Moment That Changed Everything

We all have those moments in life that split time in two: the "before" and the "after." Mine? It happened on a summer evening on Santorini, the kind of night so picturesque it could double as a stock photo for "romance." There I was, managing the boutique hotel my family owned, attending to guests, ordering wine shipments, and making sure nobody left without trying the baklava. Life was busy, predictable, and—dare I say it—safe. Or so I thought.

But as the stars blinked into view over the caldera that evening, a guest left me with a single question that flipped my world on its head. "Do you think love is a choice or a fate?"

I laughed. Not because it was a funny question but because I had no answer. Here I was, a man in my early 30s who had grown up reading Plato's Symposium and Aristotle’s musings on partnership, yet I couldn’t confidently say where I stood on arguably life’s biggest question. And it hit me: for all my philosophizing, studying, and people-watching, I had never gotten to the bottom of what I believed about love, relationships, or human connection.

That question sparked a journey—that’s what this piece is really about—the moment that changed everything. But let’s not dive straight into the deep end just yet, shall we? Let’s start at the beginning.

A Flirtation with Fools: My Dating Profile Disaster

Think of this as the "before" picture in my life. Back then, I thought I was pretty good at relationships—or at least at attracting them. After all, I had the raw materials: a cultured perspective, a great family baklava recipe, and what I like to optimistically call "Mediterranean charm." But one day, my friend Yiannis convinced me to dip my toes into online dating (Athens’s romantic skyline wasn’t exactly producing soulmates on its own). Big mistake. Enormous.

I went all in with my profile, adding just a touch too much whimsy—"Lover of sunsets, Aristotle quotes, and a perfectly folded gyro wrap"—thinking it would set me apart. While it got attention, it was the wrong kind. My matches were either critiquing my philosophical tastes ("Aristotle? Overrated.") or asking detailed questions about gyro assembly as if I were teaching a cooking class instead of looking for a partner.

Spoiler alert: That profile didn’t lead to any life-altering connections, but it taught me an important lesson about authenticity. If you're not going to show up as your full self in your dating profile, why even bother?

That Summer on Santorini: When Comfort Got Too Comfortable

Fast-forward a bit: I was back on Santorini, immersed in the rhythms of running the boutique hotel. My life revolved around people but not in ways that challenged me. I handled guests’ complaints about fluffy pillow preferences, shared tips on the best secret beaches, and played Cupid when honeymooners argued over where to eat. But when it came to my own romantic endeavors? Stagnant. It wasn’t that I wasn’t dating—I was. But every relationship felt surface-level, like eating one too many appetizers but skipping the main course.

Then came the Question.

One evening, as Oia was drenched in one of its famously fiery sunsets, I found myself sitting with a group of guests, drinking local Assyrtiko wine. The guest—a German philosophy professor, sharp as a Santorini wind at sunset—posed his question, and it ignited something in me. Not because I’d never thought about love, but because when I tried to give an answer, I realized I hadn’t thought deeply enough.

And so began my personal revolution. I started to think about the difference between flirting with a life you think you want—as I had been—and actually building something meaningful.

My Dating Profile, Revisited: How I Let My Values Guide Me

With Santorini as my backdrop and newly rediscovered introspection as my guide, I set out to reinvent how I presented myself, starting with that pesky online dating profile. If you’ve ever set fire to your life and started fresh (metaphorically, not literally—I didn’t burn down the hotel), you know how liberating it can feel. Here’s what worked for me—and might for you, too:

1. Less Perfection, More Character

If personality were perfume, my old profile was the equivalent of dousing myself in it on the first date. Now, I leaned into something more real. For instance, instead of saying “I enjoy cooking Mediterranean meals,” I wrote: “I once tried to make moussaka after two glasses of wine—my pots are still recovering.”

Takeaway tip: Be relatable, not rehearsed. Skip the clichés and present yourself as a work in progress—because we all are.

2. Say What You’re Looking For (No, Really)

My previous attempts to play it mysterious hadn’t worked. So, I got specific. “Looking for someone who can laugh through a travel delay and share a secret beach spot without putting it on social media.” This helped weed out people who weren’t on the same wavelength.

Takeaway tip: Put your "must-haves" and deep desires out there. The right person will find your radar signal.

3. Let Your Interests Reveal Who You Are

Instead of rattling off my hobbies out of context, I invited potential matches into my world. Example: “You’ll find me improvising bouzouki chords on a Sunday while my neighbors argue about the best olives—BYO opinion.” This infused my passions with a bit of color and edge.

Takeaway tip: Don’t just say what you love—paint a vivid picture of how it fits into your life.

4. Humor Works Wonders

During my revamp, I decided it was okay—no, vital—to be playful. I dropped a philosophy joke (“Can we agree Plato’s ‘ideal form’ definitely doesn’t involve pineapple on pizza?”) alongside some cheekier confessions (“I will judge your coffee order, but only after I’ve had mine.”)

Takeaway tip: Humor disarms and connects. Use it wisely, but don’t overdo it. Nobody’s here for a stand-up set.

The Lesson: Choose Big Love, Not Safe Love

After that summer, my approach to dating—and life—radically changed. I stopped asking, “Is this enough?” and started asking, “Does this set my soul on fire?” It wasn’t an overnight transformation, mind you, but it was a pivotal one. My “safe” relationships were no longer enough. I wanted partnerships where we could grapple with life’s big questions together, whether over Greek coffee or on a ferry ride to parts unknown.

And yes, I did go back to that German professor’s question about love’s nature. Ultimately, I decided it’s a little of both fate and choice—and isn’t that the beauty of it? You choose how you show up for love, and if the Fates are kind, you’ll find someone choosing the same.

From Flirtation to Foundation: My Call to You

So, my friend, here’s your takeaway. Whether you’re rewriting your dating profile, reconsidering what relationships mean to you, or figuring out your version of "Santorini," don’t settle for “safe.” Love isn’t about writing the perfect profile or landing a dozen matches. It’s about showing up fully as you are—flaws, bad jokes, moussaka mishaps, and all—and trusting that the right person will see you and say, “Yes.”

Oh, and don’t forget: If you’re ever in Santorini, the sunset is gorgeous, but the baklava by the caldera? Life-changing. Just like asking the right questions.