Love Across Continents: Lessons from Transcontinental Dating

By Karen Regn

When dates involve airline tickets, things get complicated.

Despite being swathed in dirt, sweaty, and loaded down with gear, a ruggedly handsome similarly burdened trekker sends a smile and a look heavy with interest your way. Back at the resort, the same guy stretches out on a poolside lounge chair two umbrellas down from you and you can’t believe your luck. Meeting a guy while vacationing abroad is the stuff “Eat, Pray, Love” dreams are made of. And you’ve already got a couple of great opening lines to choose from: “Say, didn’t I see you in the jungle yesterday?” or “Aren’t you dying from all these mosquito bites?”

The vacation meet-up scenario may be perfect for a romantic whirlwind hook-up, a quick goodbye, and perhaps a nostalgic friending on Facebook weeks after you’ve unpacked your bags. But if you want to see said man again, and he happens to live on another continent, this is where things get tricky. From this point on, dating involves hefty expense, jet lag, and itineraries.

I met a lovely English bloke while trekking in Malaysia. After a few Skype chats, I simply had to see him again. I didn’t care that he lived in England or that apart from a brief chat over margaritas at a gorgeous resort in Borneo’s Sabah peninsula, we hadn’t spent any time together. We had never been in the same room alone together, but we started planning how and where to make that happen.

It could have been his place or mine, but as we saw it, we had the whole world to choose from. Our first date was a weekend holiday in Edinburgh. Our second was a ten-day tour of Peru including a 50km hike on the Inca trail. Our subsequent dates were Orlando, Florida, New York City, and Ottawa, Ontario. I’ll call them “dates”, but each trip was really a series of dates crammed into a short length of time. More accurately, our vacations could also be referred to as “megadates”, each with its own highs and lows. Here’s what we learned: