Finding love in Cuba.

Los Angeles. 2000. Halloween Party. I am angry and I am leaving. I just had the last and final fight with a boyfriend. In semi-darkness, a hand holding a purple Crown Royal bag followed by a disembodied voice stops me in my fury-fueled exit. “Would you care for a fortune?”

The whimsical stranger and I would slowly fall for each other and date for the next couple of years, break-up, lose touch and eventually rekindle our connection and become the kind of friends you keep for life.

There is a pattern to every first meet. Eye contact, a smile, a faint pulse of electricity, a subconscious recognition of the other soul. The cumulative effect is always, I dig your vibe, and I want to talk to you some more!

Maybe it is New York City, the city I call “home” for the brief periods I’m not somewhere else in the world. Meeting people, specifically interesting men who I would consider spending naked happy hours with or even build a future with, has become a riddle. Yet this is never so when I’m on the road, when I’m abroad. I begin to wonder, what is the problem? Is it me? Is it this city? After conducting an unofficial survey of friends, both men and women, I’ve identified a few key points and formulated a theory: how meeting people in NYC is different than the rest of the world.

#1, The initial hello, or lack there of.

San Marco, Guatemala. 2009. Roof-Top Restaurant. I am alone in a cafe. A tall and semi-disheveled guy walks up the stairs with a worn copy of War and Peace. He sits down at the table next to me. He orders. Instead of opening his book, setting up an invisible wall of “I’m busy,” he looks at me and says hello. I looked up from my writing and we effortlessly chat for 45 minutes. Survival Spanish does not lend itself to in-depth conversations about anything beyond how to get to the bus station; intelligent company with a British accent is greeted with the eagerness of a 5-year-old on Christmas morning. On the road, I’m always open to a conversation with a stranger, handsome or not, solicited or unsolicited. Time zone and spotty WiFi connection butters clients and deadlines.

New York City. Year Round. Everywhere. In bars, coffee shops and co-working spaces, a laptop, cellphone and headphones safeguards us from an unexpected hello. And in the rare moments when the stranger catches your eye, you reluctantly pull out the ear-buds, answer the question (most often for the WiFi password) and then it’s headphones on and eyes to the screen.

Hanoi at (date) night.

#2. Common ground and shared interests.

Hanoi. 2014. Tiny plastic chairs on the sidewalk with BBQ bits on skewers. Sleep deprived and jet-lagged; I board the dreadful airport bus that shuttles you from the terminal to the plane. I am heading to Hanoi to write for the summer. Standing next to me is a handsome guy with a look of military personnel; a copy of National Geographic under his arm. He says hello. I smile. He has a layover in Hanoi tonight before he heads south to Son Doong, the world’s biggest cave. We are foreigners in a strange land. Over dinner and a quick download of where we’ve been and what we’ve done, we discover the compatibility of our travel resumes, hence one other. We are driven by the same brand of curiosity with an addiction to living life on the razor’s edge; jungles of the DRC, military escorts from the edges of Taliban country, camping in the middle of the desert with new Berber friends. We steer far from the maddening crowd. We automatically navigate towards the lesser known. Travel is not a pastime but rather a way of life.

New York City. 2015. Someone’s Apartment. I’m invited to Underground Unattached. A highly curated singles event. Twenty single men and twenty single women with shared interests and the mutual desire to no longer be single meet over dinner. There should be someone for everyone here tonight – enough spark for I dig you, let’s talk some more. The first guy I’m paired with asks, “Are you into current affairs and politics?” “Of course I am, especially with foreign affairs.” “I’m not. I don’t have a TV. I live in my own little bubble,” he says in all seriousness. Picking up on my interest in travel, he continues, “I was just in Mexico at the most amazing all inclusive resort.” The rest of the night went by in a blur of well-meaning icebreakers. The subjects that should spark conversation don’t. Have we so broadly defined these terms of personal interests into meaninglessness? Through it all, I never had a significant conversation with any of the twenty hand-selected gentlemen about travel, entrepreneurship, social good, or any of the 20+ topics that make up my core obsessions. But I did meet someone I wanted to see again. Like every significant relationship, they had me at hello. From that first moment, Christina and I knew the future for us was limitless. Two weeks later at dinner, we discover in addition to having friends in common, we were both at the same events just months prior. I showed up at Underground Unattached hoping for beard stubbles and languid Sunday mornings, but instead I found a friend and co-conspirator.

#3. Time and urgency.

Santa Clara, Cuba. 2010. Ice Cream Parlor. Was he there first or was I? After the hellos, the smiles and what brings you to Cuba, he invites me to join him and a French couple he just met on a trek to a hidden waterfall the next day. The French couple got food poisoning that night so we trekked to the water fall alone. Later we reconvened for dinner. Dancing followed dinner, and for the next year and a half, we will chase each other across four countries and countless cites. Decisions get made. There is always a bus, a flight, something whisking us away from this moment, from these pale blue eyes. Time is seized. Opportunity is never squandered.

A dime a dozen: the coffee cups and singles in NYC.

New York City. 2010. Ok Cupid. He was a German product designer and every one of our dates would last forever. We never ran out of things to talk about. Despite this, our schedules were impossible. I stare at my everyday trying to figure out where I could squeeze in an extra hour and occasionally wonder how socially acceptable would it be to set up a first date as a coffee at 8am? It took us four and a half months to go on six dates. Any sense of urgency and chemistry we had on the first couple of dates was diluted. Absence did not make either of our hearts fonder. Craving dissolved into a mild curiosity which faded into an after-thought.

All this is not to say that New York City is a curmudgeon against love. Or that the road is a easier place to date. Rather to survive and thrive in a place like New York, we must be high-functioning human beings who juggle twenty million demands at the same time. We become fractured, unable to find the time, energy or attention to successfully date. Where as we’re the opposite when somewhere new. In the city, there is always too much going on. The calendar too full; we are too guarded or preoccupied for that unsolicited conversations. The subconscious mind is always leaping ahead to what’s next, never taking a moment to see that the guy who just made eye contact with you at Caffé Reggio is someone you should stop and have a conversation with.

From Cuba, with love.