Confessions of a Traveling Male

This post isn’t by me- obviously. When Jeremy asked to write a guest post he- rightly, pointed out that my blog is somewhat lacking in the male perspective. While his experiences are very different from mine, I’m glad he chose to share such a personal story:

So here I am, a twenty-something solo traveler, gallivanting across the globe, gaining my worldly experience. And though I have been single for three years, I have made countless connections with countless women from all over the world. My relationship is with women everywhere.

I’ve never been the relationship type. Frankly, I’ve only had a couple of girlfriends in my lifetime, and only one of those was serious. And, yeah, that one? Well, it ended in a big fat fit of dysfunction. Ask my friends—they’ll tell you. Things got real weird there, for a while.

And then there were a couple more girls with whom I fell madly in love. So, how did those end? Well, you can answer that one. As I write this, I’m sitting on a train on the other side of the world. I left home two and a half years ago and I haven’t been back.

To be honest, half the reason I left home had to do with a girl.

But of course, there’s always a girl.

Some people call me a misogynist; some might call me a hopeless romantic. It depends who you ask and how well they know me. It’s a weird combination, on paper at least. But in real life, and in practice, it works. And it seems to work well.

As many men would say, I’ve been “gettin’ my flags.” And sure, yep, I’ve been doing that. I’m an independent person. And I’m a male. Cut me some slack.

But the truth is, and I don’t think I’m dispelling any myths here, men have feelings, too! It’s isolating, being on the road, traveling from town to city, country to country, meeting and bidding farewell to friends, connections and lovers.

(I hate that word, “lovers.” In actuality, though, that’s what they are. Were. Have been.)

It’s carefree and intoxicating, traveling like this. I have no commitments, nobody to answer to but myself. There’s no drama, no need to concern myself with who’s watching or whose feelings I might hurt because there’s a good chance that one of us will be leaving the other very, very soon. It’s brilliant, really. And it’s fun. Lots and lots of fun.

But then there are couples who travel together and who are so in love. And I wonder: Where did they meet? How did they become such perfect companions? It’s one thing to be in a relationship with somebody, it’s another to actually travel with them!

I’ve lost friends just by traveling with them, and learning that we simply weren’t as compatible as we thought.

No, it’s not easy being on the road alone. To the outside world, it’s the dream. And well, really, it is! (Queue sardonic laugh.) I’m 26 years old, working on a career which essentially allows me to be anywhere in the world. I get to be reckless, unsympathetic and carefree! I answer to no one. I’m friends with who I want, I sleep with who I want and I never have to explain myself.

I know. You wish you were me.

But, alas, it’s exhausting! Not because I’m fed up with the single life (I only slightly rue the day I get fed up with the single life), but because I have met a number of women with whom I have genuinely shared something special and unique with.

The sheer number of people I have encountered in the last couple of years is, well, insane. And I am picky and difficult to get along with! So when something special strikes me, I’m taken aback, and I treasure that connection.

I am an independent, strong and malleable person. I bounce back. So, in the end, inauspiciously, it’s no sweat if one of us leaves. There will always be another one.

Like I said, there’s always a girl.

But what if?

What if I stayed? What if I opened myself to the possibility of something real?

Ah, but, alas, I cannot. Because I have to go home. At some point. And thus I’m cast into forcible separation and singledom because I cannot reasonably allow myself to open up.

It’s a predicament, really. I am in a world of isolation yet I am the most social I have ever been in my life. To the women I have met, and even those I haven’t yet: I respect you, I love you and I cherish you. Really, I do. But unfortunately, it will never work.

I seem to fall in and out of love with every girl I meet, and I leave a piece of my heart with each and every one. Not in a pitiful way, but in a gracious sort of way. I am thankful for the impression that each and every woman makes on me, and the imprint she leaves, because that stays with me forever, and I will stay with them forever.

And now, remarkably, pieces of my soul have been scattered all over the world.

Born in America, Jeremy, an IT specialist by trade, packed up his belongings and left home on an open-ended trip to Australia. Two years later, he’s still on the move and exploring other countries. He is now a mobile cocktail bartender and the head writer for travelFREAK!

About The Author

29 thoughts on “Confessions of a Traveling Male”

  1. Hey Man, good post. I am hoping to fire up some traveling blog post myself as write now I just write about thoughts and perspectives at I know that it says you are blogging from the road, but does that support you financially to travel as much as you want? How do you go about being on the road for 2 years. I know the way I travel, you can easily drop 2k in a week in Copenhagen alone…

    Thanks for sharing.

  2. The only question i would like to ask you is “WHY DID YOU DO THAT ?” having fun with ladies doesn’t mean that you travel well..better try to know more and more about culture of particular country you are traveling rather than knowing ladies of that country.

  3. I couldn’t have read this post at a better time. As a GAY MALE traveler I have had MANY hooks ups, but the chance of a relationship has only arisen once & well I fell & fell hard. I spent over 5 months in Egypt with him & just recently said bye. We both knew that with my lifestyle we had an expiration date. Well now I just keep thinking “What if I stayed? What if I opened myself to the possibility of something real?”. Now I’m back on the road and it’s been tough & know it will continue to be hard. Only time will tell… & only time will heal this wound. One thing is true you do leave a piece of your heart behind & it sucks, but the moments you shared are just beautiful.

    1. As cliche as it is, Jaime, it’s true that only time heals wounds! The women I have left behind have been, well, left behind. I will always cherish them, but I no longer think of them like I once used to. It is important to remember the best, and move forward knowing that they have forever impacted your life.

  4. I like this article. Good perspective, and hopefully something my friend keeps in mind when she leaves on her RTW next year! Sounds like you’re having a great time.

    1. Thanks, Sarah! There’s a lot to consider when it comes to relationships on the road, and I could only have written this article after gaining the heavy experience that I have over the past couple of years. Traveling is eye-opening on so many levels. You really learn who you are.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top