- Cait Charles has been a digital nomad for 11 years.
- She's lived in 12 countries, visited over 30, and enjoyed romantic flings and relationships along the way.
- At 35, she's still looking for a relationship on the road but avoids getting attached too early.
My quest for a long-term partner while on the road has not yet proved successful, but it has always come with adventure.
In 2013, I took my first step into the digital nomad lifestyle by becoming an online English teacher. I knew I wanted to travel and saw this as a way to sustain myself.
Now, at 35, I've lived in 12 countries and visited over 30. I've continued teaching, started content writing, and am now working on communications and facilitation for an eco-community in Thailand, my current home.
Over the years, I've enjoyed a slew of flings and a few longer relationships. I've also learned dating lessons, including the following three.
1. Avoid premature attachment
We met at a Buddhism course in Nepal. He had long curly hair, and I had a lot of free time. I chased him for two weeks until he gave in, fell madly in love with me, and welcomed me into his apartment.
We then went about passionately ignoring one of Buddhism's core tenets: non-attachment. Attachment, the Buddha said, was the root of suffering. Testing his theory, we became fiercely attached to a future we quickly planned out — one replete with copious amounts of curly-haired children.
Within months, our quest to do the opposite of what the Buddha had taught brought us face-to-face with another core tenet of Buddhism: impermanence.
After we argued our way through nine countries and eventually broke up, we ended the relationship with a hand-in-hand walk around the Buddhist stupa in the heart of the neighborhood where we first met. It realized that premature attachment to a vision that doesn't yet have a strong foundation doesn't work.
This happened 11 years ago, but it's a lesson I've had to learn a few more times since.
2. Find friendships in failed relationships
And then there was Moishe. Ah, Moishe, like a breath of fresh air when you fear not being able to breathe anymore. In this case, partly due to a new respiratory virus that was spreading — it was 2020, and the pandemic had just been announced.
We met on Nomad Soulmates, a dating app for digital nomads under the most surreal of circumstances. All flights were being canceled, and the world was in panic.
We seemed to mirror each other perfectly. We were both longtime travelers and secular Jews from the US. Both of us wanted a life partner, but not kids — a near impossibility to find within our demographic. Best of all, we were both obsessed with building community by hosting dinners, workshops, and other types of meetups.
To bridge those 13 timezones and COVID masks that separated us — I was living in South Korea, and he was in Pennsylvania — we did what any logical couple dating online for five months would do: we decided that I would fly across the world and we would do the whole "quarantine" thing together.
We rented a one-bedroom apartment in Pennsylvania Amish Country for three months, where we could hear the clop-clop of horse hooves passing by our house at all hours.
It turned out Moishe and I had one more major thing in common: a shared tendency to get ahead of ourselves. You would think we could have avoided putting the cart before the horse in a town where it was constantly on display properly, but we managed it.
Just a few days after moving in, it became clear that we weren't a match romantically. However, we continued to work from the same home and be each other's sole social contact for the next three months.
Although my hopes of finding a long-term partner were quickly dashed, this story has a happy ending. We both ended up moving abroad again and now share a social network.
For me, the lesson here — aside from the obvious one about not making forever plans before you actually meet — is that there's a richness to be gained from having the flexibility to transform a failed relationship into a top-notch friendship.
3. Go with your gut
I was just getting out of another failed relationship when I went on my first Tinder date. We met in Florida when I was visiting my dad en route to Mexico for a Central America adventure — a trip that swiftly canceled after the first time I saw him take out the ponytail elastic and let down his hair. His good looks convinced me to stay.
Though we had a strong initial connection, there were obvious underlying issues from the get-go. While I've always been fascinated by relationship psychology, he was skeptical. We also didn't share the same long-term goals; for example, he was set on staying in Florida, while I had no intention of returning to the US full time.
For a year, we tried to make something work that was doomed to fail. Spoiler alert: It failed. It turns out that if you enter a relationship thinking, "This probably won't work out," then you're probably right.
But I have no regrets. The experience taught me to prioritize the potential for a healthy relationship in the future over the impulse to settle for a less-than-ideal one in the present. Nowadays, I let go more gracefully early on when I see that a connection is unlikely in the long run.
My biggest takeaway from these nomadic love affairs has been that it just doesn't bode well for a relationship — or for your heart — to get ahead of yourself by taking big steps and making big plans early on. When you're dating on the road, the temptation to do so is strong, and connecting at a speed that would seem crazy in the "real world" is commonplace.
Connections often feel more intense, too, because we digital nomads exist within a bubble of transience and time limits. There's a feeling of urgency that pushes us to connect faster.
It may be fun at the moment to move in with a guy from the internet, make lifelong plans with the curly-haired Buddha, or spontaneously cancel your onward travels, but if you don't live inside a romantic comedy movie, these are not ways to build an actual stable relationship.
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