Dating While Traveling :: An Anecdote

A picture of the sunset in Kruger National Park, South Africa, one of the first places we went to

An Intro

I was writing in my journal about the ending of a recent “relationship” and decided to write it in here with the hopes that it helps someone out. I put “relationship” in quotations because from the moment I met this person I was honest about what day I would be leaving the country and for that reason she had no interest in putting any labels on something that was clearly ending from the beginning.

So I’m currently in a cafe in Cape town, a pretty beautiful spot with dark grey walls and yellow wooden chairs that contrast the walls really well. It sits alongside a canal that reminds you out of something from Amsterdam it’s a beautiful spot for sure, and super inspiring for writing.

Picture of where I’m writing this from, at Shift Waterway House

So where did it all start?

Back in December knowing I was going to South Africa I got Tinder’s international upgrade where I could change my location, and I start getting matches in South Africa. I got along with one of the matches quite well and she offered to meet me at the airport when I arrived. When I got off the plane I was looking for someone wearing pink with pink luggage. We had talked for a bit, but I wasn’t ready for how attractive she was in real life she had these beautiful long braids, a huge welcoming smile with these beautiful, full lips and her overall mannerisms where something that reminded me of the Japanese word Kawai. She was cute and somewhat reserved yet with a warmth that made me want to start hugging her right there. We ended up spending the last month traveling around South Africa, we got mugged together, we saw blood hungry hyenas, lions and even a rino in the bush, we did wine testing in the mountaineous wine region of Franschhoek, (check out my Instagram for pictures of this) we drove through the waterfall ridden green mountains of Mpumalanga. We had a lot of fun times in the last month and now it’s over.

Beautiful Waterfalls South Africa - Emgwen
Maybe the most impressive waterfall this trip,in Emgwenya

So why did it end?

I’m still not entirely sure why to be honest, but if I were to attribute it to any single thing it would be communication. At some point it got difficult for us to communicate our feelings back and forth to each other and the more one of us shut down the more the other would shut down and as you can imagine that turned things sour rather quickly.

I’m not mad at her, and I only wish her the best, I just recognize that the ending must come and now seems like a good time for it to happen, rather than prolonging the inevitable. I wasn’t always like this though, where I thought logically about this stuff. I’m actually reminded of a few weeks I travelled through the Philippines with a girl I had met there. We explored these incredible islands together and were around each other for nearly the entire time experiencing things together. The night before my flight back, I asked her if I should extend my plane ticket. I was still on holiday from my English teaching job in Vietnam and it would be easy to change the ticket. She was brushing her teeth and without even looking at me she continued to look in the mirror while she said “I think that’s a bad idea.” At the time I chalked up here directness to her culture, I figured it was her being Chinese that made her more cold and calculating about these sorts of things. Now I actually respect what she did. Our time had come, we didn’t have that much in common, and we had a good run. It was likely only going to get worse as we drug things out. She had the maturity to see that and so she ended things before they went south. Furthermore she did so in a way that was completely unambiguous. There was no confusion in my mind as to what she meant and what our future looked like. I think maybe now I’ve become her with the cold calculating reasoning about travel relationships (Jesus, the college Loren would be so revolted thinking I’ve turned into one of those people 😂).

Beautiful Waterfalls - Phillippines- Camiguin
One of the waterfalls from Camiguin, Phillipines. I think I’m really into waterfalls (queue the TLC song)

So how do I feel about it?

A part of me is bummed out about it but another part of me knows that it’s time. This isn’t my first impassioned travel fling and it likely won’t be my last. I recognize that these things are going to end, I recognize that the emotions I feel for that person are inextricably linked to the emotions of the experiences we had together. There isn’t any divorcing those two things the excitement and awe I felt watching the sunset while giraffes and lions were wandering around us, the ecstacy I felt after our 3rd vineyard wine tasting while driving in the bus through the vineyards, I can’t divorce those emotions from my feelings for her. All of those emotions summate together. When I think of it, she almost begins to personify those places and experiences for me.

There was a point yesterday right after we ended things that I was walking to another hotel to stay the night, right here in Cape Town. I was listening to music in my headphones and I could see the sunsetting over table mountain, there were these beautiful pink and light blue colors in the sky peeking through the buildings. I felt so alive. I wanted to cry, I was remembering the times we had together and thinking about how it was over and I felt so alive. The colors of the sunset were brighter, the music in my ears was clearer, the smells in the air were stronger. It was as though all of my senses had been heightened and I realized that I loved that feeling. I love that heightened experience of your heart breaking (or micro-breaking in this case perhaps), it makes you feel so alive.

Right now, I’m sitting here working through my emotions and finally outlining my quarterly goals and re-aligning on my big dreams in life for the quarter. I’m excited about the future. I’m excited to get serious about the gym again, about eating healthy again, about getting a grip on why I’m doing what I’m doing and the direction I want to go. The last month has been this ecstatic whirlwind of incredible experiences, experiences I’ll never forget and I don’t want to ever forget, but it’s over and I’m only going to sour those memories by trying to hold on.

Updates & Reflections

1/24/22 Update

I went back to the hotel she was staying at, she was still there. We made up, admitted that both of us are horrible at relationships but will work things out for the next week or two until I go to Durban 😂

1/26/22 Update

We started arguing again about nonsense and ended it, pretty sure it’s final this time…. should’ve re-read this article before deciding to try it again 😬. I went on a date with another woman last night, felt somewhat emotionally detached, performed horribly when it came time. Maybe it wouldn’t be a bad idea to drink a bottle of Amarula about it and take some time to myself. Or continue trying to find a replacement in any woman I find attractive, not sure what I’ll be doing.

We drank a lot of Amarula together I don’t know if I want to drink Amarula again for a while, it’d be cool to keep that drink as a nostalgic thing to only drink once a year or so and think back on my time with her. But I really don’t think I can do that, I love Amarula. It’s been a lot of text without photos so going to add a photo of me with a bottle of Amarula.

3/24/22 Update

Currently writing this from Rome, (this isn’t the best digital nomad spot in the world, but here’s my Rome guide if you’re coming). I had a situation in South Africa that required me to leave very suddenly so I got a ticket to Rome and here I am. I got back together with the girl at the beginning of February and we travelled around South Africa together for the last month and a half. We drove through the Garden Route, an incredible part of the country. We had a lot of great times, we both made a lot of mistakes, but at our best we had grace and understanding.

A short video from Mossel Bay, on the Garden Route

I miss South Africa, and I miss her. I don’t know if we’re not meant to be together or if I just lack the commitment to make it work. I believe she could commit to me, and if it were up to her she would make it work. I’ve had an incredibly unhealthy relationship with women for a long time now. I use women to feel validated and valuable. When first meeting a woman I need to sleep with her as soon as I can to feel like she likes me. If she doesn’t sleep with me then I’m insecure and feel as though she could be using me. After she sleeps with me, then if we still continue to talk, then I want her to love me (or at least think she loves me). In this I can further validate myself and feel secure that I’m not going to be used and that I “won” at the end of the day. It’s pretty f***ed up.

While I have had deep connections with women, the prerequisite for this was always sleeping together. I am working now to flip that script a bit. Honestly, I’m taking a break entirely from pursuing women but when I start again I want to be able to take the time to get to know them first, instead of sleep with them as fast as possible then get to know them. I’ve used sex as a symbol of acceptance & validation from women, proof that I am enough, that women want me, that I’m not being used by women for money and or emotional support.

This was a huge fault in my logic. Dating & romance requires vulnerability and I can’t try to overcome that vulnerability through sex & “conquering” a women’s heart. It hurts others and it hurts me. It gives too much power to women I barely know, and it diminishes the connection I have with women to a game. The women are not humans with needs, emotions & desires they’re pawns in a game I designed to feel better about myself.

6/13/22 Update

A video taken from a Cenote in Tulum, right next to Playa Del Carmen

I’m thinking about updating this article regularly, with updates on my dating life as I travel. Italy was a pretty tough period for me. I spent a lot of time walking in introspection, figuring out what was going on with my dating life, and life at large. I figured out quite a few things while walking alone around the beautiful architecture of Rome. A couple weeks into my time in Rome, I found an opportunity to be part of a pilot reality TV Show. I figured the show would help me grow this brand so I went for it. Then the show brought me to beautiful Mexico (follow me on Instagram, if you’d like to stay up to date on the show).

So (for the hundredth time), I got back together with the girl toward the end of my time in Italy. We decided we would do the open thing since we were long distance (queue the scary music). Then while on the Reality show pilot, I met someone. I was honest to both people involved, and while it didn’t feel like the best move in the world, I continued things with both of them (man I’m gonna look like a dirtbag if this show gets picked up). At one point I was seriously considering getting married to the woman from South Africa. I talked with her dad about it and everything.

The show ended, and I talked the girl from the show into staying with me for a bit before she went back home. We spent a pretty awesome week together in Playa Del Carmen (check out my nomad guide here) and during that week it was pretty clear things weren’t going to work out with the gal from South Africa. We were a world apart in more ways than one. I also learned so much about myself and relationships with this new girl from the reality show, and I was excited about everything I could continue to learn with her. Shortly after that week things ended again with the South African gal.

This time it’s gonna stick (how many times have I said this?😂). Things are getting more and more serious with the girl from the reality TV show. I can see myself staying with her for a while, we disagree on some pretty major philosophical / spiritual things, however I think I need someone like her at this point in my life. Maybe it will last another week, or maybe another year. I don’t know. I know that since being with this woman I will never view relationships the same, the depth and insights I get from being with her are unlike any other woman I’ve ever been with and I genuinely appreciate her and what we have.

I don’t have the slightest clue on how to successfully run a relationship, if you haven’t already picked up on that. If nothing else, I hope this article gives you an idea on how to not date as a digital nomad 😂.

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