I actually think dating while travelling is a really good idea. Here’s why.

March 06, 2024

From where I’m sitting on the mountain, I can see all of San José, Costa Rica’s capital, stretched out in front of me. City lights flicker, lighting up the basin of the valley. Skyscrapers stand firm but are dwarfed by the mountains that flank the city. Each of these peaks represents a piece of the country I’ve been exploring in recent weeks: Santa Ana, Ciudad Colón, Puriscal, Escazu. The sky has darkened after sunset and now I’m looking at planes flying through the night and touching down on the runways straight ahead of us in the distance. Out loud I wonder where they’ve come from: the U.S.? El Salvador? Germany?

I’m here with Pablo, a friend of a friend and a local to the countryside area where I’m staying for the next month and a half. When we met at a bonfire, he offered to take me on a motorcycle ride and show me one of the local lookout spots. Now, here we are. We cruised through sunset around mountain curves, past dimly-lit countryside homes, through a cloud of evening mountain mist, and up a steep dirt road to this view of the capital.

I decide that the airplane we’re looking at is coming from somewhere in Europe. Germany or the Netherlands because I’ve seen heaps of tourists from this area of the world. Costa Rica seems to be a magnet pulling them in droves. Of course, I can’t know for sure and it doesn’t really matter. I’m just appreciating this night which I couldn’t have organized on my own. There’s so many tours marketed to foreigners here in Costa Rica and many of them I’m uninterested in. What I’m really after is getting a glimpse of what those from here would be doing on any average day. Going out with a local (when there’s a genuine connection/interest, of course) is a pretty good way to do that. Actually, dating has often enhanced my experiences abroad for that reason.

When you say yes to invites that come your way, you get to know the culture on a deeper level.

I wouldn’t have been able to see this side of the country had Pablo not offered to take me. For one, I would have no way to get here and since it’s not advertised or talked about anywhere, I’d have no way of knowing this place even existed. You have to live here to have that knowledge. Also, while Costa Rica has tours for many of its beautiful hotspots, many of them are just well outside of my budget and a little too neatly curated for what I’m looking for here.

One of my 2024 goals is to travel more… and to travel ethically. One way I think I can do that is by listening better and taking the time to see a destination’s quieter side which would be existing just as it is regardless of my presence as a tourist. On this particular night with Pablo (and ones that follow it), I learn about Costa Rica’s stance against smoking in public. I find out about an earthquake that rocked the town in the late 1980s and consequently left the church standing hauntingly abandoned. I also learn about contraband coconut booze which I probably shouldn’t drink (but do anyway). I expand my vocabulary as well with (so many) slang words which a tour guide absolutely wouldn’t teach me. Then there’s details on which place serves the best chicharron, why certain stores are crowded at particular times of the month, how Ticos budget for a life lived in one of Latin America’s most expensive countries, and why toucans play where they do. These are all details that don’t necessarily make or break my trip, but they do reveal more about the place I’m in.

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Dating while travelling is a good idea because you learn so much more about the culture when interactions are genuine, engaging, and driven by curiosity. (To be clear, I’m only talking about when interest is sincere. I’m not suggesting using anybody as your tour guide!) And time spent practicing a second or third language is never time wasted, in my opinion.

However, that only happens when you ask the right questions. When you do, the answers could even change your worldview.

One evening, I ask Pablo to name just a few things that would secure a happy, successful life. His responses are notably different from what a North American might say. Firstly, to live as long as possible. Secondly, to appreciate quality time with his son on the family farm. This sheds light not just on personal values, but national ones.

I come from Canada which (generally speaking) puts career growth, finances, education, outdoor adventure, and ladder climbing first. I’m here in Costa Rica whose motto is “pura vida,” (pure life) and which boasts being the home to one of the world’s blue zones—areas where the general population tends to live longer thanks to a mix of lifestyle choices and environmental factors. Now, a local is telling me he wants to live as long as possible and appreciate family relationships and the pocket of the country where his family lives. Years ago, when I moved to Latin America, my priorities shifted along with my change in location. I value quality of life, adventure, friendships and creativity above many things. Conversations like these reaffirm an ever-changing worldview and values I now prioritize.

P.S.: Goal-oriented approaches might not serve you here.

In societies that often highlight and value monogamy and partnership and even more so marriage and kids, it can be hard not to treat dating with a goal-oriented approach. Especially if you’re in your thirties, like me. Been there.

I say this as much to myself as others: when we treat people or places with an attitude of “What can this experience do for me?” we’re going in with a tunnel-vision approach that closes us off from potentially awesome outcomes. Most of us don’t treat friendship with this goal-oriented approach though. Instead, we let those connections evolve naturally. I think the same should be done for romantic relationships. So, I try to scrap the goals and be present instead.

Parrots couple

On a blistering-hot day in Costa Rica, I’m outside sunbathing with my friend. Both the 50 SPF and beers are flowing. I’m keeping an eye for parrots flying overhead and maybe a toucan. My friend, speaking her mind, blurts out that she doesn’t get me. If I don’t plan to have a long-distance relationship or move to Costa Rica, why date here at all?

My answer to her still stands: I’m here to learn what the culture is really like and like to make genuine connections when I travel. Plus, when I go anywhere, I want to be open to returning to that place for longer periods of time given that I work remotely and that’s an option for me. One of the best ways to see if a destination is a fit culturally, is to establish and explore a social life. That includes dating… for me anyway. Do I connect with locals at all? If so, who? Where? And why? I actually think dating during your travels is a really good idea because it’ll help you answer those questions.

This article is part of the
Issue 3


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