A few years ago, I found myself sitting on a weathered stool in a dimly lit bar in the Faroe Islands, surrounded by sheep skulls, ancient fishing nets, and the smell of smoked cod wafting from somewhere in the kitchen. I had ventured to the rugged, rain-drenched archipelago to chase a lead for a historical fiction novel I was drafting, but what I ended up chasing instead was my breath, after a local man offered me what I can only describe as fermented shark in a shot glass. It’s called hákarl, and it’s both a traditional delicacy and a dare wrapped into one tiny, unassuming cube of fish. But that’s not even the craziest part of this story.

If you think about it, the Faroe Islands are like the dating world in miniature: remote, unpredictable, and thrillingly, frustratingly hard to navigate. And just like stepping off a metaphorical cliff in your romantic life—whether it’s attempting a first date after a bad breakup or confessing feelings to the friend you’ve been secretly pining for—this place had a way of catching me off-guard and holding me captive, even when I was tempted to run back to the safety of my Nantucket routine. Here's what I learned about braving the unfamiliar, whether it’s a wild new destination or the uncharted waters of connection.

1. Getting Lost Is Half the Point

The day I arrived, my first task was to rent a car and figure out how not to drive off a cliff. Seriously, the roads in the Faroes look like every car insurance agent’s worst nightmare: narrow, winding, and flanked by sheer drops into the frothing Atlantic. With no GPS signal and exactly one gas station in a 30-mile radius, it was only a matter of time before I got lost.

The same thing happens in relationships, doesn’t it? We set out confident we know exactly where we’re going, only to hit unexpected roadblocks and wrong turns—a misunderstanding, an awkward lull in conversation, a weird text that ends with “lol” when nothing was remotely funny. But trying to control every detail is exhausting, not to mention counterproductive. Sometimes, you’ve just got to embrace the detours.

When my car sputtered to a stop outside a village I couldn’t pronounce (Sandavágur? Sørvágur? One of the “-vágurs”), I ended up having a picnic with two farmers who didn’t speak a lick of English but happily shared their dried lamb and showed me how to whistle at sheep. It wasn’t on my itinerary, but it was better than anything I’d planned.

Dating takeaway: Stop obsessing over your “ideal type” or planning the perfect date down to the minute. Say yes to the unexpected and let the little disruptions surprise you—you might just stumble onto magic.

2. The Unfamiliar Looks Scary Until You Try It

Let’s get back to that fermented shark for a moment. Hákarl isn’t just an acquired taste; it’s a badge of survivalist honor in the Faroe Islands. The shark meat is buried underground to ferment for MONTHS, and when it emerges, it smells like ammonia mixed with regret. Every instinct I had said, “Step away, Oliver, before this ends in tears (or a call to medical assistance).”

But something happened when I worked up the nerve to try it. Was it delicious? No, absolutely not. I wouldn’t wish it on my worst enemy. But it left me oddly exhilarated, like I’d conquered a tiny piece of my own fear. And maybe that’s the point.

It’s no different when you take risks in your relationships. Asking someone out, apologizing when you’ve screwed up, opening up about your needs—they’re all the emotional equivalent of eating fermented shark. Sweaty palms, racing heart, that nagging inner voice yelling “Abort!” But here’s the thing: courage, like taste buds, adapts the more you use it.

Dating takeaway: Stretch outside your comfort zone. Say the brave thing, even if your voice shakes. Worst case scenario? You cringe about it later with your friends over wine. Best case? You surprise yourself and deepen the connection.

3. Lean Into the Isolation

Let me tell you: there is nothing quite as humbling as standing on a rocky outcrop in the Faroes, with 100-foot waves crashing below you and not another soul in sight. Sure, the vistas were cinematic—brooding cliffs, endless sea, cloud-tufted mountains—but they also pressed on me a kind of loneliness. It reminded me of returning to Nantucket after college, unsure if the world I grew up in could still hold me, unsure who I even was apart from it.

Sometimes we don’t talk about the loneliness of dating—the unavoidable stretches of time when you’re single and everyone around you seems coupled up, or those moments when you’re in a relationship but still feel... not quite known. But you can either resist those quiet spaces or embrace them as fertile ground for self-discovery. On that cliff, I chose the latter. I let the isolation wash over me, and I unearthed something surprising: clarity.

Dating takeaway: Solitude isn’t something to fear or fill. Use it to reconnect with yourself. Whether you’re single or partnered, being comfortable alone makes you a better person to be with.

4. Be Ready for the Unexpected Yes

On my last night in the Faroes, I was convinced I’d explored everything worth seeing. But the innkeeper—a sprightly woman named Margrethe, likely descended from Viking royalty based on her bone structure alone—asked if I wanted to join her and a few locals on a late-night boat ride. My inner New Englander hesitated. It was raining (again), I had a 5 a.m. flight, and I didn’t know these people. But something told me to say yes.

We ended up rowing under a cliffside grotto lit by candle lanterns, the walls echoing with the ancient Faroese ballads Margrethe sang as we drifted beneath waterfalls. It felt like magic, the kind you can’t orchestrate or replicate, the kind you only find when you choose to trust the moment.

It’s the same with relationships, really. The unexpected “yes” can lead to the experiences that rewrite your life. Yes to meeting someone you’d normally overlook. Yes to vulnerability. Yes to staying a bit longer when you’re tempted to leave.

Dating takeaway: Lean into spontaneity. The safest choice is rarely the one with the best payoff.

Keep Your Compass, But Welcome the Waves

So what’s the craziest place I’ve ever been? Sure, technically it’s the Faroe Islands—a wind-swept fever dream of cliffs, sheep, and fermented shark. But really, it’s anywhere outside my comfort zone, whether that’s standing on a lonely outcrop in a foreign land or navigating the highs and lows of connection with another person.

The key, in both life and love, is to stay open: to the detours, the risks, the silent moments, and the unexpected "yes." It’s not about perfect plans or guarantees—it’s about leaning into the waves and trusting the uncharted to lead somewhere extraordinary. After all, as the Faroese say (probably—I couldn’t understand most of their words), life is too short to always play it safe.