What’s scarier: walking into the lion's den or texting someone “What are we?” Don’t answer just yet, because in my experience, the two feel strikingly similar—palms sweaty, heart racing, a strong desire to sprint in the opposite direction. Fear: it’s a sneaky companion in all our relationships, one that whispers, “Maybe just stay safe. Don’t risk it.” And yet, I keep risking it. I keep leaping. Why? Let me tell you.

The Fear Factor: What Keeps Us Frozen

I’ve faced a lot in life: moving countries, running a hotel on an island during peak tourist season (imagine managing 300 different personalities while praying no one complains about room service delays), and once hosting a wedding reception where the bride’s ex showed up—but nothing paralyzes me quite like being vulnerable with someone I care about.

One fear stands tall above the rest: the fear of disappointing someone—of letting them see the clumsy, imperfect, occasionally too-philosophical version of myself and having them decide, “No thanks, I’ll pass.” Growing up in Greece, my family taught me to be charming (it’s how you get repeat customers). But charm only skims the surface; vulnerability dives deep. And diving? Well, I’ve never been the best swimmer.

But here’s what I know for sure: fear doesn’t just stop us from connecting with others—it stops us from connecting with ourselves.

Why I Keep Choosing the Leap

So why do I keep showing up despite the nerves, the awkwardness, the stutters over dinner when someone asks me about my favorite childhood memory? Why practice the art of relationship acrobatics knowing every leap could lead to a crash landing? Simple. Because every leap teaches me something about myself and—when I get it right—about love itself.

During one summer on Santorini, I had a whirlwind romance with someone I met at a seaside taverna. She was French, sharp-witted, with a laugh that made strangers turn their heads. I remember her saying over dolmas, “You’re so mysterious, Dimitri. Why don’t you let people in more?” That stuck. I realized that in my fear of being judged or misunderstood, I was building walls instead of bridges. Spoiler alert: the romance faded like a summer sunset, but her question stayed. What’s the point of connection if you’re too guarded to truly experience it?

Since then, I’ve made peace with the idea of discomfort. Awkward pauses on dates? Fine by me. The occasional “seen” message with no reply? It’s part of the game. Every time I wade into this terrifying, unpredictable sea, I come back swimming a little stronger.

How to Confront Fear Without Letting It Win

Over time, I’ve figured out a few tricks for dancing with fear rather than letting it step on my toes. Here's what I’ve discovered:

  1. Name It
    Fear hates being named; it’s like a vampire exposed to daylight. “I’m afraid of rejection.” “I’m scared of being too much—or not enough.” When you name the fear, you rob it of its mysterious power. Write it, say it out loud, tell your cat if you have to. Just get it out of your head.

  2. Make It Specific
    A vague fear feels suffocating, but a specific one? You can work with that. It’s no longer “I’m scared to date.” It becomes “I’m nervous they won’t laugh at my jokes” or “I’m afraid to talk about my messy family.” This makes solutions possible: test the jokes, edit the awkward family saga, or just decide that humor and family quirks are part of your charm.

  3. Turn Small Wins Into Big Momentum
    I used to think courage came in dramatic, leap-from-the-cliff kinds of moments. Turns out, courage is quieter, often sneaky. It’s texting first, even when it makes your stomach do a backflip. It’s sharing a thought you’ve been mulling over instead of defaulting to safe small talk. Those small wins? They build your bravery muscle. By the time fear shows up at your door, you’ll already be holding a solid shield.

  4. Keep Curiosity Over Certainty
    Socrates always said, "The only true wisdom is in knowing you know nothing." (Yes, I am a walking Greek cliché, quoting philosophers in everyday life.) Fear thrives when we assume the worst. Instead, stay curious. Ask yourself, “What if this goes well?” or “What could I learn if this doesn’t work out?” Curiosity opens doors; fear slams them shut.

  5. Don’t Wait for Confidence
    Here's the inconvenient truth they don’t teach in school: confidence comes after doing the scary thing, not before. I wish I could say running a boutique hotel made me fearless about interacting with strangers—it didn’t. But it taught me this: when discomfort becomes familiar, it becomes a little less scary every time.

Love as an Act of Courage

Let’s get real: no amount of self-help hacks and clever motivational quotes will make fear disappear entirely. Love—whether it’s a first date, a one-year anniversary, or the mature kind shared over sixty years—is inherently risky. It will always feel a little like dangling from the edge of a cliff with no parachute. But here’s why I keep climbing anyway: life is too rich, too unpredictable, too full of stunning surprises to sit safely at the top without ever taking the dive.

Love is dropping the mask. It’s choosing to be seen. Warning, though: sometimes you’ll land face-first in the sea. Sometimes, like many heroes of Greek tragedy, you’ll get burned chasing the sun. But sometimes? You’ll surface, breathless, laughing, with hands outstretched to the person who decided to face their fears right alongside you.

Final Thoughts: You’ve Got This

To anyone standing on the edge of fear, hesitating, wondering if it’s worth the risk: start small. Send the text. Say what’s on your mind (even if it’s messy). Embrace the awkwardness. Most importantly, remember this: The worst-case scenario isn’t that you’ll fail—it’s that you’ll stay stuck, forever wondering what could’ve happened if you’d had just a little more courage.

Fear will always be part of the package, but so is joy. And if Greek summers taught me anything, it’s that life is too short not to dive headfirst into both.