A girl in every port? An honest account of a long-term traveller's search for love on the road

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A girl in every port? An honest account of a long-term traveller’s search for love on the road


Full disclosure: This post contains affiliate links. ?

Ever since my viral post about the 29 life lessons learned in travelling the world for 8 years (over 2 years ago), I've started to get more and more questions about finding love on the road.

How can a long term traveller have a girlfriend? What about leaving a wake of broken hearts behind? And the one I'd hear far too often… aren't you just like a sailor with a girl in every port?

I reached my 10 year travel anniversary over the summer and got even more people asking me about it, and it's a post that I've been promising to write for a while. The problem is that while I could give my story, and conclude with a hopeful outlook, it still wasn't the happiest story, which is why I have been postponing writing it for so long.

Everything has changed now though, because after ten whole years of crossing deserts, climbing mountains, hiking trails, flying, driving, dancing and getting trains across the world, I've searched everywhere for that special someone, had genuinely given up… and then finally found her.

A girl in every port?

It was a long road to get here though, so I think I should share it, so that you can get the full picture!

I went to an all-boys Catholic school, followed by four years of a mostly male dominated engineering degree, so I was still uncomfortable talking to girls when I went off bright-eyed to start my travels in Spain. It took a lot of work, but I finally got over my shyness. My technique is very simply to not think so much about what could go wrong, and just talk to people, and slowly started to feel more comfortable in my skin.

A year in Spain (and then finally a few years later, definitely my time in Brazil) gave me the Latin spirit it took to make me a much more outgoing person. So, now I could finally confidently talk to everyone, interesting women included. Problem solved, right?

Not quite – my second country after Spain was an incredibly intensive working position in a hostel in Rome, but there was an Italian girl I kind of liked, and I invited her out for a coffee.

Things were going well, and then I finally mustered up the courage to invite her out for a real date. She laughed at me though, clarifying by saying “Ma dai, Benny! Hai una ragazza in ogni porto!” (Come on Benny! You've got a girl in every port!”) suggesting she didn't want to be nothing but a notch on my bed that I'd forget within a week or two.

I was really disappointed at this reaction – I had only been in 2 or 3 ports by then, none of which I had Don Juan style romances, and I had a crush on this girl for months actually.

Every day for a world traveller... in the minds of most people (not true)

This view of every traveller being a womanizer (I imagine some people see me as looking like in this staged posing photo on the left all the time) is a little unfair, and I see it as another stereotype that I have to put up with like all all the Irish people drinking myth.

I actually find it ironic because this mid-20th-century concept of sailors going around screwing girls each time they pull into port, leading to modern “girl in every port” cynicism is precisely one reason why I did not have a girl in every port!

The huge cynicism (except perhaps for the other extreme with ditsy naïve girls, which I'd avoid) means all potentially interesting girlfriends in one “port” may automatically turn you down before you've had a chance to shine.

A broken heart…

But even if I'd meet a girl who'd believe me that my goal in life isn't to “collect a flag” in each country, she'd see that I'm only in her city for a few months, and very quickly point out the fact that I honestly said I was leaving in a few months, and that I'd do nothing but leave her with a broken heart if we got attached.

Essentially, I would meet someone I like and on hearing that I have a ticket out of the country in a few months, they'd look at me as if I had announced I have terminal cancer and 3 months to live, in terms of relationship prospects.

This really emphasized the stark differences in how travellers see the world. When I visit a country, and see how easy it is to pack a few things, get a cheap flight and move across the world, then I always knew that if I found someone special, the possibility was there to simply go back and stay longer (I've gone back to Brazil four times, and to Spain five times in my travels, although never for love), or see if perhaps she would like to travel with me a little. But so many settled people believe that a traveller will never come back, or presume he wants nothing but superficial relationships.

Relationships (of all kinds) are the reason I travel in the first place, and what defines my unique style of travel.

Transitioning into travelling with someone is very hard if you are socializing outside of expat groups though. There are many stories of people finding love on the road and making it work such that they travel together, but almost always this is from two people who are both in travel-mode already themselves when meeting, so they already had the momentum.

The language learning theme to my travels meant that most friends I was making were settled locals, unlikely to be open minded to dating a traveller.

One exception to this though was when I started to date a girl at the start of my third year travelling. Things were going in such a direction that I seriously considered settling down and living with her, even though I wasn't crazy about where she lived. But she was getting ready to travel herself (in a different direction to me), and one day made it clear to me that she actually was looking for just a few weeks of fun and that our time was done, and explained that she herself actually has… a man in every port.

Since I saw a future with us, this really hurt me.

One reason that I hate people casting the girl in every port stereotype on me, or presume that I leave broken hearts all over the place, is because I know precisely what it's like to be on the receiving end of a traveller not taking your relationship seriously. I'd never intentionally do that to another person.

The confusing male/female dynamic

So after a while, I just had to accept that this lifestyle is simply not conductive to meeting the girl of my dreams. After a few years, it was getting tiresome when I'd try to genuinely get to know someone, see potential for a relationship and have it shot down immediately because of things that weren't true about me.

Added to everything else was the major problem that I kept switching between vastly different cultures so quickly, and how you compliment a girl in South America, North America, France, or the Philippines, for instance, are vastly different.

Whether you hold the door open for her or not may make you come across as anything from an anti-feminist macho, to inconsiderate and ungentlemanly, depending on which extreme you may be with, and what action you try to remember to take where you are, which is highly influenced by local culture. This adds a whole new dimension to the already complicated dating scene.

But frustrations with meeting a significant other are not unique to me and my lifestyle. This is something we all face at some stage, and some of us struggle with it for life, for a host of reasons.

I've even managed to randomly meet Neil Strauss, the guy who wrote “The Game” – the book that brought the underground pick-up-artist scene to the public eye. He's actually a really nice guy when you talk to him!

Such movements sprung up in the first place though because many people simply grow up in an environment that doesn't allow them to confidently talk to girls, and deal with this as best as they can. Sometimes a few techniques may finally give them the confidence to break out of their shell.

I consider pick-up-artistry as mostly a placebo however, to find that “trick” that will make girls like you, or give you the confidence to talk to girls – I never used a chat-up line, and simply opted for “Hi, I'm Benny”. I'd say it with confidence, because I've introduced myself to enough people to not be afraid that it'll be the end of the world if they don't like me.

If I have to put on a show just to get a girl's attention, I'd find that exhausting, so I prefer to start as I mean to go on. I would genuinely tell a beautiful and interesting girl that I speak Klingon if it happens to come up in the first conversation. If that's a dealbreaker, why hide it?

The years went on, and no real romantic relationships flourished…

When you bounce around alone, the fact that you haven't found the love of your life isn't really that big a deal for the first year and you're 21… or first four years… and well, a little annoying after six or seven years…

But it takes its toll. I'm in my 30s now and hadn't had the chance to explore a deep long-term relationship with a girl due to the restrictions of the travel lifestyle. It starts to get stressful to think about it, especially when you are occasionally somewhere you are subjecting yourself to stressful situations already, but have nobody to talk to intimately, to vent off that frustration.

I wasn't lacking in confidence to meet girls. But nothing truly deep would ever come out of anything. The best I'd get would be to go on a few dates with someone over a few weeks, but not develop deep enough feelings in that time.

I was starting to accept that I may just have to continue this lifestyle until I am done with it (I've been saying for a while that I'll only be travelling for another 2 or 3 more years, and the difficulty in finding someone special to share my life with was contributing to this), and then when I'm maybe 35 and settled, I could start dating without this annoying “you've clearly got a girl in every port, or plan to leave me with a broken heart!” presumption from the onset. Seems like a huge lifestyle change to make just to get rid of an annoying stereotype.

I was still hopeful about meeting a girl on the road though! But I was made extra cynical due to one more negative experience while in Berlin.

I met a girl I got along with really well, and thought we maybe had a future because of how much fun we had together. But she said that she wasn't looking for that at all, and that she saw a world traveller (any world traveller; who was irrelevant) as an adventurous fling, and not really long-term relationship material.

It reminded me that more often than not, interest would spark because of aspects of what I do (travel, language learning etc.) rather than who I am. You can't be the Indiana Jones/Jason Bourne character 24/7 – every one of us has hang-ups and vulnerabilities we'd like to talk about. Unfortunately, this doesn't fit in with reality if that impossibly perfect image is what someone is looking for.

Since I read the situation so wrongly, this disappointment had been the straw that broke the camel's back and I had pretty much decided for good that I was going to stop trying to find Ms. Right, travel for a few more years, and then when I settle (wherever that would have been…) try to date like a settled person, even if that may not have been ideal for me.

You find it faster when you stop looking for it so hard

As well as unfair stereotypes, it was of course my own fault for messing up otherwise interesting possibilities.

On occasion, when I would meet a girl I kind of liked, I'd mess it up by trying too hard to show the best of myself in the brief social event that may be the one time I have to make an impression. The problem is that when you overdo this, it doesn't come across as being so authentic, and that would in itself mess things up.

So when I stopped trying so hard, that's when I finally did find the girl of my dreams, and the one I'm happy to travel the world with and spend many hours each day with (between studying and speaking whatever language I'm learning/improving of course).

About 5 months ago, I crossed paths with a lovely girl who I hung out with for several days, and as pretty as she was, and as friendly and sweet as she was… I intentionally stopped myself from trying to win her over.

We hung out as friends, with no other agenda at play, and she got to see the real me because of that. She unfortunately had to travel on, while stayed put, but we kept in touch and were honest that we really liked one another. So I went out of my way to spend longer with her very shortly after, saw that she was the kind of special person I see myself with long term, and now… she is travelling the world with me, and someone I'm absolutely sure that I'm in love with 🙂

She's not a travel blogger, polyglot language learner, or rich tourist, but we still found a way to make this very strange lifestyle work, and she's been living with me in Spain (who do you think was my camerawoman during the Japanese tour of my apartment?) and coming with me to Japan and beyond next year.

The details of how we met or who she is, where she's from etc. aren't something I'd write on a public blog post like this, but early January of next year I'll share my travel itinerary (including visits to the UK/US etc.) for most of the year, and if you can make it to, or live in somewhere I'm going, I'll be happy to introduce you to her in person, and she or I can tell you all about it 😉 [If you want to make sure you won't miss that update, don't forget to subscribe to the email list in the top-right of the site!]

If you are travelling yourself, or still trying to find that special someone while settled, just remember not to look too hard for him/her, and focus on living your own life so that you find someone who is in synch with that, you don't have to change anything about yourself to be comfortable with them. I had travelled the entire world for a decade, and then finally met my match when I least expected it, and when she was the one travelling, rather than me.

As you can see in the photo at the very start of the article, we make a cute couple as we sit on the beach in Valencia watching the sun set. I'm glad to finally share this story with you all, now that it has a happy ending!

author headshot

Benny Lewis

Founder, Fluent in 3 Months

Fun-loving Irish guy, full-time globe trotter and international bestselling author. Benny believes the best approach to language learning is to speak from day one.

Speaks: Spanish, French, German, Italian, Portuguese, Esperanto, Mandarin Chinese, American Sign Language, Dutch, Irish

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