Michael DiLeo

A common set of questions I've gotten from people about my travels are about the topics of romance and relationships while traveling, such as how relationships even work, what are people doing around romance, and how do you handle the temporary nature of everything when you're constantly moving. It is true that it can be difficult to maintain relationships when you're constantly saying goodbye. That does not, however, seem to be stopping people. I've had quite a few conversations with people about it, so I figured I can share some of them here along with some of my own observations.

#travel #relationships #digitalnomad

How people seem to view romance, relationships, and sex while traveling

There are a few different spectrums or styles of romance that I've noticed while traveling the past year and a half. One type that I encountered is people who are just on vacation or are short-term traveling and want to sleep their way through as much of the trip as possible. A lot of it may have to do with being away from your own watering hole, so you know you won't run into them again. Other factors, I believe, are that they're on vacation and want to have a good time, as they're having fun anyway. Additionally, who doesn't want the “We met in Paris” story of their relationship? I mean come on, we all do.

Continuing on this concept is the idea of novelty. New places, new experiences, new people, new experiences with new people. If that's what someone is looking for there are plenty of people to find along the way who are either looking for or are open to the same thing. It's fun and exciting, but there's also the aspect that there's a time limit. The eminent end of the trip makes the feelings stronger and even bitter-sweet. There are a lot of mixed emotions that can intensify how your connection with this other person feels. As if you are both racing the clock. This applies more to shorter term travellers than those who are traveling for longer.

Amongst those I met who were nomading longer, hooking up didn't seem to be as much of a priority. It still happens, of course, but it could be that it got old, or the novelty wore off, or people got tired of constantly saying goodbye. It's not like people weren't open to travel relationships, of course, but it didn't seem to be as high of a priority compared to the short-termers, vacationers, or recent starters. I did meet a few long-term travel couples. Most of them already knew each other and set off on the nomad life together. I did meet a small number who met while traveling. In those relationships, I saw two styles: one in which they traveled together the majority of the time, and the other being that they would travel together for a while, then split and do their own thing for a bit before meeting back up. However, it was quite rare to meet couples who met while traveling and kept traveling together. The majority of people were single, but pretty much everyone said that they'd like to find that person to travel with. That's easier said than done for a variety of reasons.

The obvious reason is that, duh, you're traveling. The problem with travelers is that they travel. They have different goals and wants. I think that there are some less obvious reasons as well. The main one is that dating or finding your match doesn't get much easier. You do meet a lot of open, like-minded people when you are in environments where nomads congregate, but matching with someone still needs more than that. So, the normal problems of dating still apply. However, you do help your odds a bit because you're placing yourself in an environment to meet people with similar interests and values. The other obstacle that comes into place is that this pool of people is smaller. While there are plenty of other nomads, it's not the equivalent of endless swiping in a local city by any means. Unfortunately as well, the odds of saying goodbye are pretty high.

Even if you are spending several months in a place and meet someone doing the same thing, people usually have different ideas on where to go next. It's not like you can't meet up again later, and many do, but you are saying goodbye and it can get tiring emotionally doing it over and over again. But that doesn't mean to stop; sometimes you just need a break for a bit. You make wonderful and beautiful relationships of all types with people while traveling. Each of them will hold a special place to you, so sometimes people are worn out from it for a bit, but become open again after taking an emotional rest.

I've noticed within my own self is that the excitement feeling of travel relationships was a lot stronger when I started and felt fresher, but over time that both wore away and wore me down. I had to learn to say goodbye and be comfortable with it. One of my biggest lessons while traveling was becoming ok with things ending, whether that be trips, experiences, or relationships. Of course it's not like your connection to the person is over; you can still call and reconnect. At some point I realized that I may have become calloused. I didn't always put as much effort into getting to know people quickly. I normally am quite good at it. I used traveling as a way to practice opening up and doing so gives other people permission to open up as well. I became very close with others very quickly because I “went past the bullshit and opened up” as someone once told me. I'm glad that I have a helpful tool to do this.

My favorite thing to use to get to know people quickly is a card game called “Big Talk.” It's not really a game, it's a set of open ending questions that people can answer and works great in small groups. I tried it once in a larger group, but there's a mismatch with openness in a larger group like this.

I'll give you an example by picking a random card and how I would answer it.

What advice would you give yourself five years ago?

I would tell myself to be more open to relationships with people that were already around me. I was probably too afraid of “shitting where I eat,” so to speak. I'd also tell myself to not be afraid to leave a job that was a bad fit. I actually got fired from a job after working for two years that I should have left 6 months in. I was miserable and progressively couldn't mentally function in my role from it, but I was afraid of the job market at the time. Maybe also the idea of doing the change felt like a lot and I didn't want to have to relearn everything and get on-board at a new company. That would probably be my main advice. It was a hard-learned lesson that had a lot of suffering along with it that could have been avoided.

I strongly recommend the Big Talk card game. I've had it with me for years and it has helped me deepen the friendships that I already have and create rich, new friendships quickly. My main tip for it is to expound on the reasoning behind the answer that you give. Answer the question, then explain the “why” behind it.

I think that I need to get back into doing this with people. Being open is a necessity for long term travel, I believe. We need connections with others as human beings, so when you are frequently moving on and making new connections with people, having only shallow interactions all the time can make you feel isolated even when surrounded by others. At least it does for me, anyway.

How have cultural differences played a role in romantic relationships

Culture plays a not very surprising role in how relationships work when you are traveling. One example that happened with me is that I was with a woman from South America and I thought I was being pretty affectionate for a gringo, but she told me she wished I was more affectionate that my lack of affection was hard for her. I love that stuff, so you don't have to ask me twice, but I was a little bit confused as to what more I could do. I was just out of ideas. Latin American culture is so much for expressive in the romance department than gringo-land is. I also heard from old friends who moved to the US that this cultural difference was hard for them.

There was another funny difference that I discovered in South America – opening doors. I'm raised in the southern part of the United States, where opening doors for women is considered good manners, along with saying “sir” and ma'am, though I believe the latter may be becoming less popular since people in other places take it as you calling them old. I was discussing the opening of doors culture with some Argentinians and they viewed the practice as almost patronizing or treating them like children. Now, I like doing small gestures like that and, again, I was raised in a place where not teaching your children to do so was raising them with bad manners, so I thought it was quite funny. No one really seemed to have much appreciation for the practice down there. It's not like anyone was overtly offended by it (except for some people from California at a few points), but very few Argentinians I spoke with seemed to like it. If anything, they were a bit confused by it.

But aside from this, cultural differences while traveling are pretty much the same as they are anywhere else. The main difference is that you're more likely to encounter them since you're meeting people from all over the world. The good thing, though, is that you become more aware of differences and can better take things in stride and laugh at the misunderstandings, as there will be a lot of them. It's not different while traveling vs at home.

While I wasn't a super-dater while traveling by any means, the connections I made along the way helped me to become a better person. Each person, whether friend or romantic, left me being a better person. I still mentally cringe at some gaffs that I made along the way and I remember several times that I hurt someone's feelings. I learned from it. But overall, I think that mantra stays the same. Say “yes” to opportunities, walk through open doors, and enjoy the ride of life with all that it brings.