My Sordid Attempts at Finding Love on the Road

by Nora on July 3, 2017

“But Nora, with all this moving around from place to place over the last 10 years, what about finding love on the road? Do you have relationships?” I was asked by the host of a ridiculously popular travel radio show in a live-to-air interview.

“Oh yeah! Lots of them!” I replied eagerly, before getting a hold of myself and saying “You know, I’ve had a few partners who I’ve traveled with along the way.”

Afterwards as I reflected on the interview and the fact that I’d basically just told 11 million or so people that I’M EASY, I launched into a reverie about the relationships I’ve had in the last decade of full-time travel, and how finding love on the road – the kind of love that sticks – as a full-time traveler just ain’t easy, as much as I’m loath to admit it.

finding love on the road - or not

The timing was ironic; a few hours after that radio interview, I parted ways with a fellow I’d nurtured a lovely relationship with over the last eight or so months. Our future: uncertain. Minimum time apart: five months. Reason: lifestyle differences. I had a house-sitting gig in Japan with my name on it, and he had an empty bank account and a job in the U.S. for the summer season that promised to pad his wallet and make a reunion possible.

I’ve been here before. Saying goodbye to passionate lovers I don’t want to say goodbye to, without any knowledge of when or where (or if??) we would meet again.

Although in theory I’m a fan of couples taking time apart and each doing their own thing as the beautifully well-developed individuals that we all are, it hasn’t always worked out so well for me (see “take two” below as an example of how absence apparently does not always make the heart grow fonder). So I’m nervous about our time apart, because anything can happen. My life has a funny way of swerving left when I’m preparing to turn right, and five months is both a short time and a long time for some twists and turns to happen for either one of us.

What seems to have smacked me in the face with this latest reflection on my romantic history is how bloody hard it is not just finding love on the road – but finding compatible love on the road. And when your lifestyle is as “out there” as being professionally homeless (as I am), compatibility takes on a whole new meaning.

In fact, the more I look back at my relationship history over the last 10 years, the more I see that lifestyle compatibility has been the downfall just about every time in one way or another. Have a look for yourself:

lovers on the road do make great photographers! ha ha


The Travel Saboteur: Finding Love on the Road, Take One

First, there was Kelly. I started dating this adventure-loving fella a year before I sold everything to travel full-time. And he came with me for the first few years of full-time travel. He didn’t have a digital career (nor the makings of one, as I was busy developing). But he was pretty quick on his feet and made some money along the way. Problems began when it became apparent that he didn’t really want to live a nomadic lifestyle. After unconsciously digging his heels in along the way a few times, running out of money, and eventually planting some defiant roots in Australia, I left him (and his new Aussie girlfriend!) there and moved on.

For more on what it was to experience my first breakup on the road and how travel affects relationships in general, read Breaking up While Traveling.


Fidelity Bites the Dust: Finding Love on the Road, Take Two

Next up was my Swedish Squeeze. Six months of casual romance turned into a serious romance with no direction. He had some financial savings, but no direction – in career, location, and ultimately, life. Which is why, when we were spending a few months apart pursuing individual projects (mine being the Ultimate Train Challenge), his lack of direction directed him into the arms of an old friend who would nine months later become a co-parent with him.

I wrote about my Swedish Squeeze and the philosophy of Romance on the Road when we parted ways, and then again in the throes of heartbreak in a post called Being Thankful in Grenada.


Insta-Family: Finding Love on the Road, Take Three

My next major relationship was a game-changer for me since it involved declaring the Caribbean island of Grenada as a home base, as that was where he and his adolescent daughter lived. I enjoyed many things about having this home base, but the relationship was fraught with problems, not the least of which were very different career paths and a complete lack of support for my online career (which was often deemed as “playing on my computer” even though it paid the bills for both of us).

Read about my decision to adjust my lifestyle to be with him in Time for a Change: The Professional Hobo Switches Gears, and about our ungraceful breakup in The Day I Was Dumped Via Instant Message.

finding love on the road

Lost in Transition: Finding Love on the Road, Take Four

A couple of years later while living in Peru, I struck up a romance with a visiting American. He was in the midst of a big life change, and his relationship with me was the final kick in the pants he needed to quit his job and sell everything to move to Peru. Although we were pretty compatible in a variety of ways and he had the makings of a travel-friendly career, we just didn’t work out.

By this point I started keeping quiet about my attempts at finding love on the road – I thought perhaps writing about them was a form of jinx, so I didn’t write about him. It still didn’t work out.


Lover-Boy: Finding Love on the Road, Take Five

Another year and a half passed, then I met J (another American) in Ecuador. At first glance, we epitomize compatibility issues in the departments of career, finances, and age (he’s….ahem….considerably younger than I). But despite our best efforts, we couldn’t deny a connection that went deeper than these incompatibilities to reveal a whole other playing field of what it is to relate to and communicate with another. While living at the retreat centre in Ecuador, we had a blissful life, compatibilities be damned. (It’s also worth noting that his talents in the realm of working with plant medicine created an underlying tapestry of compatibility). Outside of the retreat centre “bubble”, it’s another story full of unanswered questions; one that has me sitting on a plane and wondering when or where (or even if) I will see him again. Wondering when we do meet up again, if there’s enough glue to hold us together despite outward incompatibilities.

finding love on the road feature pic


Compatibility: Can’t Live Without It. Heck, Can’t Live With It Either

Okay, so maybe my attempts at finding love on the road haven’t exactly been sordid, as the title of this article indicates (and how I felt after declaring my looseness to 11 million of my closest friends in that stupid radio interview).

The most compatible partner for me (logistically) would be somebody with an established location independent career and a lifestyle to match. As much as I know that no romance is perfect behind closed doors, it seems to me that location independent couples have some big advantages when it comes to being on the same page in career and lifestyle. And with double the manpower and often complementary skills, many of these wonder-couples do admirably well career-wise. (Check out some of my Financial Case Study interviews with couples to see for yourself). 

But I’d like to think there’s more to the picture than just career compatibility, and that I’m indeed capable of finding love on the road that doesn’t come in the shape of a travel blogger or digital nomad. Maybe emotional compatibility, complementary personalities, and even physical compatibility (yeah, you know what I’m talking about) counts for something.

Or maybe compatibility in general is an overrated concept, designed by dating services. In “take four” I found somebody who was fundamentally compatible on many levels, but it still didn’t work.

Or maybe I’m just grasping at straws for the moment in the hopes that my relationship with J can supersede our outward incompatibilities.

But no matter how you slice it, finding love on the road – the kind of love that sticks – is difficult. It’s certainly getting easier, with increasing numbers of people designing lifestyles that allow them to live and work on the road. In the meantime, however, I still find myself in the world of nervous goodbyes and hopeful reunions. There’s not much more I can do at the moment than trust in the process and see what happens.

And so, it is.


{ 16 comments… read them below or add one }

1 Rob July 3, 2017 at 10:44 am

In my world it just happens. Things click and off you go but it does take compromise…
Maybe “compromise” is the wrong word? We had to adjust what “we” wanted to get a better fit into each others lives.

Combining two lives into a partnership in a nomadic way of living seems harder than doing it in a “normal” town type setting.
I think you need both luck & the ability to compromise so you both get mostly what you want.

I realize I’m not saying anything you don’t already know, I’m just lending support because I know it can be done.

Good luck!


2 Nora July 4, 2017 at 12:12 am

Wise words, Rob! With each experience under my belt now, I’m learning more and more what ingredients are required to make it work. And like you say, adjusting your expectations through communication about what you want – both as individuals and as a couple – is very important.


3 Lewis LaLanne July 3, 2017 at 1:11 pm

This is a situation that probably isn’t talked about all that much.

It’s really cool that you’re open to talking about it and I wish you the best on your quest.

Maybe someday your experiences combined with advice fellow nomads who have found love on their traveling journey will create a guide that helps people to shortcut the process and side-step the drama that is easy to fall into when emotions and hunger take the steering wheel.


4 Nora July 4, 2017 at 12:18 am

Hi Lewis,
An interesting idea! But love is a many-faceted thing, and very different for everyone. I wonder if a “guide” to successfully finding love is even possible to create!
Many of the challenges I face finding love on the road aren’t all that dissimilar to doing it “at home”; the problems are just compounded and often exaggerated, making it more difficult overall.
I think finding love (anywhere) is mostly about knowing yourself, what you want, and being able to communicate effectively. Now…knowing, and applying knowledge are also two different things. 😉


5 John Lewis July 4, 2017 at 5:11 pm


The current problem with love and compatibility in our current world is that – just maybe – we have all been sold on this idea that it should always be heavy sighs, smiles, and longing gazes across rooms at one another. That this is enough to sustain any relationship. Seems as though every book, show, and movie revolves around this theme.

Reality bites us in the ass when that romantic partner then proves that they have human failings after all – and you do, as well. How dare we be regular people? Why aren’t our lives like in the movies we like?

Now, at one time, people didn’t seem to have this problem as much. In my opinion, it’s because *they worked together for a commonly-agreed upon goal.* They were a unit. A team, where each knew that they had to work at it each day to succeed, and that some days were not going to be as smooth as others – but BOTH worked together at it. They persevered.

Maybe…just maybe, that’s what you need to find. Someone who isn’t perfect, but wants to persevere with you.

Okay, enough pontificating from me. Hope this is some help to you, as you contemplate your navel in Japan.


6 Nora July 6, 2017 at 6:05 am

Hey John,
Indeed, I think we’re a society heavily influenced by media and movies (showing us the “perfect love”), and in combination with out instant gratification mentality (“it’s not working NOW, so it’s over”), it’s a lethal cocktail when it comes to the hard knocks of enduring the tough times in a relationship.

Way back when, when couples stayed together, it’s because they couldn’t divorce. So they worked through their problems. And if they couldn’t work through them, they still appeared married for all intents and purposes. Was their relationship actually working or satisfying on any level? Who knows.
Now, we can divorce. Sometimes, for very good reason. Other times, because it’s easy.

Thank you for your pontificating!


7 Paul July 5, 2017 at 5:57 am

This post hit home, feel the same way as a nomad.


8 Nora July 6, 2017 at 6:08 am

Hey Paul,
I’m sorry you can relate (because it sucks), but I’m also glad you can relate (because it means I’m not alone/crazy)! 😉


9 Elizabeth Houck July 6, 2017 at 10:32 am

Nora, it sounds like creating a location indy dating site may be in your future!
Enjoy Japan!


10 Nora July 6, 2017 at 10:09 pm

What an idea! Hmm…I wonder if something like that already exists. An interesting concept! 😉


11 Steve Tambosso July 8, 2017 at 10:48 am

Interesting read Nora. It is coincidental that I find myself in the very same position as you, (as I’m sure does many a nomadic traveler). Having just retired to a life of full time travel I sigh at the prospect of doing it alone. Friends of mine have all chimed in chorus “Ah but Steve…don’t worry….you’ll find her on the road”, to which I chuckle and shake my head. You know that I’ve traveled extensively in my life already and I know that meeting a life partner on the road is a lot easier said than done. I completely agree with you in that regard. For me compatibility rests on many issues but being a best friend to your mate is key. I also agree with you that open communication is paramount. Without it, even casual friendships can fall apart. You can work around a lot of other issues if you have a deep underlaying friendship with your partner. Regardless of where my travels take me alone, I will continue to wander, because that’s what I was born to do. I will document my travels through the lens of my camera and share those images with the world through my website. I share your angst Nora (if ‘angst’ is the correct word). Regardless, I’m still excited at this new chapter of my life and I remain optimistic that somewhere on the road is the woman who holds the other half of my amulet. “The Wandering Fireman” wanders on………….


12 Nora July 9, 2017 at 6:15 am

Hey Steve,
Although partners (or at least, compatible ones) can be hard to come by on the road, you can take comfort in the fact that there are more and more people taking to the road – either in retirement (like you), or with their businesses/jobs (like me).
And it’s also worth noting, that although I’ve had a few strikes in the love department along the way, I’ve also had 5 solid relationships in the last 10 years, which isn’t a bad track record! Also, I’ve rarely actually felt lonely even when I’ve been without a partner.
So wander on, my friend. Wander on!


13 Chris Backe July 9, 2017 at 10:29 am

What podcast was this?

I met my now-wife while traveling… though I’m quick to point out ‘expat dating’ is a very different world from ‘nomad dating’. We met and married as expats, and we now live as nomads.

It happens… but it really does require a great match… you’re not just matching on the physical or mental level, after all. Emotionally you’re invested in each other as your confidant and person-that-looks-out-for-you as you travel through places where you need to rely on each other…


14 Nora July 10, 2017 at 12:32 am

Hey Chris,
I don’t understand the podcast question. I didn’t make a podcast (or rather vlog, because that’s what I’m doing these days) out of this article….but maybe I should! 😉

Great observation about the level of reliance on one another when traveling. That’s why, in my initial musings about relationships on the road years ago (, I suggest that travel accelerates the natural progression of a relationship. I think this is a big reason why – this reliance and inter-dependence that can happen is not always easy to cope with or get through, if the proper foundations aren’t already in place.

You also make a great point about dating as expats vs nomads. Although these two groups would share many of the same challenges on the whole, it’s probably a bit more complicated with the nomadic lifestyle.


15 Chris Backe July 10, 2017 at 5:03 am

Sorry, *radio show*, not podcast. Did you notice a boost in traffic after the show went live?


16 Nora July 12, 2017 at 12:54 am

Hey Chris,
Oh right! Sorry. I should have made the connection.
Although this is a very popular show (Rudy Maxa’s World), I don’t generally find that live radio “appearances” convert terrifically well to traffic. So I didn’t notice a huge boost in traffic. But to be honest, I also didn’t check, as I literally got on a series of planes right after the interview and for the next three days!


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