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Notes On Trying To Date At Home But Live Nomadically


Photo courtesy of Ravenwood.

“Is this always how it’s going to be?” I was going on another one of my “little trips” again, and Joe wasn’t happy. The inevitable was near. Typically it happens about three or four months into a relationship. Everything is going well, I finally think I’ve found someone who understands my passion for travel, and then it’s over before it started. Just as I realize how much I like them, they realize how much I love travel. I huff. “Joe, you know I’m a travel writer. It’s not like I’m leaving you to go on vacation with my friends all the time. It’s a job and a lifestyle.” Joe rolls his eyes. I can see his mind spinning like a pinwheel. He is picturing me laying on sugar sand beaches, ordering caviar and oysters from the St. Regis room service, getting a massage in a private cabana and possibly jotting a sentence of two down on my blog in between glasses on Champagne. And while there are often opulent perks, there is also much time spent interviewing, taking notes, working hard to get the perfect photograph and waking up before dawn to get pitches sent, Tweets scheduled and articles drafted before the day’s exploring. I’m not complaining by any means, I’m just saying it’s not the cake walk everyone makes it out to be and that being successful in the travel industry is hard work. Not to mention the fact this isn’t a job I applied for. It was a position I wanted so badly I created it and made myself a valuable asset. Joe didn’t see this, though. Most guys I dated didn’t. They didn’t seem proud of my accomplishments or impressed that I had started my own travel business, but instead seemed resentful. Then Joe said something that made it clear he didn’t get me at all. “Jessie, you’re not living in real life. Adults work real jobs. They go to offices. They have health insurance. They don’t gallivant around the world from city to city writing about it in some online journal.” Joe didn’t need to say it was over. With a statement like that, I couldn’t even believe we’d ever begun. This wasn’t the first time this had happened to me, and I knew it wouldn’t be the last. The men I met always seemed excited at first. I seemed independent, interesting, worldly and always had something to talk about. They saw themselves getting to go on trips with me and living vicariously through my adventures. Then reality sets in, and the questions begin. “You’re leaving again?,” “Where are you going this time?,” “Are you going to do this forever?”. And once they realized it wasn’t just a phase but an actual lifestyle and career choice, that was it. Before Joe I dated a guy named Mark who also had a love of travel and the outdoors. For awhile it seemed like he understood that my blog was a real job, one that allowed me to live in an apartment in Brooklyn, own a car, pay off my student loans and have a smartphone. While he had a corporate accounting job working 60 to 70 hours a week in an office, on weekends we would take trips to the nearby Catskills and Poconos, hiking, kayaking and find quirky shops and cozy bed and breakfasts so we could get our travel fix while spending time together. One day while we were hiking Mark seemed preoccupied. After what seemed like an eternity of silence he finally looked at me and asked, “Do you think I should quit my job?” I was confused. Despite the fact he worked long hours Mark seemed to love his job. He made a lot of money, his boss treated him to nice dinners and he got along well with his coworkers. Where was this coming from? “I look at you and see you’re out exploring the world and having these experiences you’ll remember for the rest of your life. My dream is trek the Appalachian Trail, but I don’t think my boss would give me enough time off to do it. So I’m thinking maybe I should just quit.” This was something I hadn’t yet experienced in my nomadic dating life. While it was typical for the guys to get sick of me leaving or look at me like a restless child, it was something new to actually inspire someone else to pursue their dreams beyond what society deemed you were supposed to do. I had to stop myself from getting too excited, though, as I realized he had to make this decision on his own. “Mark, that’s ultimately up you. I think the world needs two kinds of people. The kind who uphold structure and keep the gears of society turning and the kind who march to a different beat and keep the world guessing. Maybe you’re a little bit of both. But you have to decide for yourself.” This constant discussion continued for another month. He would go back and forth with his decision. One minute he hated corporate life, talking about how it held him back and kept him from doing the things he really enjoyed. Then an hour later he would be talking about how hard he worked to get to where he is and how fulfilled his job made him feel because he was good at it. During these times he would look at me like it was my fault he was going through this turmoil, as if I was pressuring him to make a decision. In reality, I would have been completely content with spending weekends together and continuing to travel on my own. That week I flew to Trinidad & Tobago to do some articles on outdoor recreation and cultural offerings. Mark was scheduled to pick me up at the airport for a weekend together at my house, cooking, drinking wine, watching movies and just relaxing. However, when I arrived into JFK International Airport nobody was there to get me, and all that I had was a single text that read “Sorry. I think I have strep throat.” I later found out that Mark did indeed become stricken with strep throat — as well as an epiphany that our lifestyles were just too different. While certain family members and close friends have views that I need to stop traveling and settle down, I don’t agree that that’s the solution. Why should I stop doing what fulfills me for someone who may or may not come around anytime soon? Despite my hardships in trying to find a work life balance — or a life travel balance — I don’t believe that giving up on seeing the world and living my life to the fullest is the answer. While I don’t know how my love story will end, I do know that travel has made me a strong and independent person and has supplied me with enough memories and experiences to keep me smiling with nostalgia into old age. I hope that one day I find someone who shares the same lust for life and realizes the importance of appreciating the moments we’re given. Do you find it difficult to date while traveling? Share your story in the comments below.

About Jessie Festa

Jessie Festa is an New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

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  1. Alyssa on at 2:01 pm

    Came upon your blog via Twitter – the title intrigued me πŸ™‚ Ugh, this makes me so worried for my own relationship as I continue to make travel a lifestyle!

    Maybe you should try to get the next guy to come on one of your trips with you? One day you’ll find the right guy who is just as nomadic as you!

    I look forward to reading more of your posts!

    Yours in Travel,


    • jess2716 on at 11:58 pm

      @Alyssa- Yea, it seems that every guy wants to travel but most are too afraid to take the leap to do it as much as me. Which is fine, although I would love to meet someone who shares my passion for seeing the world. That being said don’t let worrying about relationships keep you from traveling. The right guy will respect that it’s something you’re passionate about and will hopefully admire you for it πŸ™‚

  2. Lance on at 8:50 pm

    Unless you are gone for weeks at a time I don’t understand this. There are so many “traditional” jobs that require people to travel. I’m the son of a truck driver and my dad was on the road sometimes for five or six straight days. Pilots, traveling salespeople; there are lots of jobs that require people to travel a lot. Being a traditional newspaper journalist in addition to my travel blog I’m not able to be on the road as much. But I’m fortunate in that my wife loves to travel and would be happy to travel constantly. I’m sure there is a guy out there who loves to travel.

    • jess2716 on at 7:42 am

      @Lance- I sure hope so! πŸ™‚

  3. Caroline Eubanks on at 3:47 am

    Preach on. I definitely agree with this. If you say this isn’t a “real job,” you deserve a smack in the face. I have been toiling over the same experience for a while now.

    • jess2716 on at 7:36 am

      @Caroline- Agreed! πŸ™‚

  4. Amanda Kendle on at 2:39 pm

    Keep doing what you’re doing Jessie!! Either you’ll meet someone who understands it or down the track you might want to travel less or whatever – it’ll all work out somehow – but you’ve got to be true to what you want to do – not “get a real job” just because lots of people think that’s the way it should be!

    (I don’t get to travel as much any more, because of my 3-year-old, but I work for myself and have been asked when I’ll “get a real job” too – and my answer is – I hope I never have to!)

    • jess2716 on at 3:55 pm

      @Amanda- Thanks for the words of encouragement. You’re such a great example of being able to do the travel writing thing and have a family. Very inspiring! πŸ™‚ It’s so true you need to be true to yourself and everything will fall into place.

  5. Monica Suma on at 2:51 pm

    Love this post, good points, also unfortunately true. People still don’t understand this is not a whim, it’s a job, and to be able to travel and write about those stories, you almost have to work double when you’re home.

    • jess2716 on at 3:56 pm

      @Monica- I know! I try to explain this to everyone. When I’m not traveling I’m working around the clock to make up for lost time. It’s a job that’s also a lifestyle, and we’re essentially small business owners promoting our brands and the destinations we visit.

      • Drew Meyers on at 4:00 pm

        “we’re essentially small business owners promoting our brands and the destinations we visit.”

        I’d love to skype for a few minutes on that — it (potentially) plays into something I’ve been thinking about awhile.

  6. Drew Meyers on at 3:00 pm

    Sounds like we need a traveler’s dating website for us crazy ones who are obsessed with travel..

    • jess2716 on at 3:53 pm

      @Drew – If you start one I will definitely join! ha

      • Drew Meyers on at 3:57 pm

        Hmmm….another business oppty to explore? lol…there is definitely an angle to take that could turn oh hey world into a cool dating site for travelers. Not sure that’s the direction I want to take it though…though I do absolutely want to find the right girl who loves travel as much as I do.

  7. Sherrydayne Edwards on at 3:33 pm

    Hey Jessie!

    Stumbled across this article on twitter and it caught my attention- and it was beautiful written and also very true and down to earth. But I just want to say one thing- love- will come at the most unexpected time, and its going to be the hardest thing you have ever imagined you could ever go through. There is going to be one person who loves you enough to allow you to spread your wings, on your own, and will encourage you too. But the best thing is, is that when you come back ‘home’, wherever that may be, they will be waiting for you, they might even surprise you on a journey. They will love travel just as you do, and will join you on some trips, if you let him, but also allow you to have the freedom to continue your independent travels. πŸ™‚ It doesn’t matter what your circumstances are when it comes to love, you will always find a way to make things work πŸ™‚ Keep enjoying your travels πŸ™‚

    • jess2716 on at 4:29 pm

      @Sherrydayne: Thank you so much for the thoughtful comment! Very inspirational and something very important to keep in mind, especially when you say “It doesn’t matter what your circumstances are when it comes to love, you will always find a way to make things work.” That can sometimes be hard to remember but it’s very true πŸ™‚

  8. Brenton on at 9:14 pm

    Hi Jess. Came across your article in the twitterverse, and I clicked it because I am at the rudimentary stages of ‘dating’ with a girl from overseas. It’s strange because upon returning home I relate the most to those who are currently doing what I had done: people on their working holidays who are passing through for a transient period.

    So you’ve questioned the traditional ways to obtain sustenance. Why not evolve the traditional views on relationships? Travelling taught me that I can’t invest, or rather, it is far too risky to invest in one person, and it’s much better to spread that load amongst a greater number creating that network and friendship group.

    Why do you need to date? What the hell even is that? I know that I struggle to conform to that approach. For me dating encompasses meeting various people in various situations while extracting and contributing for your needs and fulfillment. If it isn’t seamless then you’re dating…

    • jess2716 on at 10:29 pm

      @Brenton: Love this idea! I’m actually surprised nobody has brought this up yet — or that I hadn’t thought of it — as I’m always talking about how as solo travelers and backpackers we’re changing the way people “traditionally” travel. Thank you for the insightful comment!

  9. Becky on at 2:50 pm

    This is a beautiful story and one that I’m positive will end with a “happily ever after”. Continue living your life and following your travel career and I hope that you will find a strong, encouraging relationship if that’s what you want or become confident in your solo status, if you choose to embrace that instead. I don’t believe there’s a one-size-fits-all solution for lifestyles, relationships, or fulfillment in life but I wish you the best as you set out on the journey to find the balance that works for you.

    • jess2716 on at 3:34 pm

      @Becky: Thank you so much for the encouraging words. Over the years I’ve definitely seen many instances — especially in the world of travel bloggers — that one size definitely does not fit all, which is refreshing πŸ™‚ Happy trails!

  10. Chris @ One Weird Globe on at 8:46 am

    As someone who met his wife while traveling (and spent years dating while traveling), I’d say it’s a unique challenge to each person and their location(s). I love Drew’s idea of a travel-dating website (maybe add the platonic side of things beyond simply networking too? I love making new friends). The reality is a little harsh: travelers live in a different world than settlers (e.g. people who pick an area and settle in it, take a job, or the whole notion of ‘putting down roots’). We’re no more tied to a place than need be, and some of us are allergic to the idea of ‘putting down roots’…

    It’s probably clear from your dating profiles you’re an avid traveler with a busy schedule (if it’s not, it should be!). That’ll weed out some of the homebodies or people that don’t quite get it. You might also mention your need to be professional doesn’t require ‘growing up’ by taking an office job or submitting to the world’s idea of a schedule…

    • jess2716 on at 5:54 pm

      @Chris: I have no clue why but I’m JUST seeing this. Totally agree with everything you said — especially that growing up doesn’t need to equate to an office job. It does get annoying that people seem to think this way, though. Luckily now I’ve found a guy who doesn’t, and actually is proud of me that I built my own business from a passion.

      PS: Had no idea you met your wife while traveling. Inspiring! πŸ™‚

    • Drew Meyers on at 6:13 pm

      Hey Chris
      We’ve scrapped Oh Hey World, rebranded to Horizon, and have solved the “why connect” with “to find a place to stay”.

      Would love any feedback you have on this new iteration:

      PS: I had no idea you met your wife traveling either. So awesome.

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