I have yet to hear of another ‘digital nomad dater.’ If you have, keep it to yourself. I rather cherish the idea of being the first to have publicly done so. I am sure many people have moved to cities to meet potential partners. Others surely have digitally nomadded and found romance. 

However, I wonder if anyone has yet been foolish enough to publically announce their intention beforehand. 

A little over a year into my journey, I reflect on the experience and thought I’d share.

We’ll start with the journey’s unique characteristic, intentionality. Being intentional consistently puts more pressure on me. 

Most conversations with family and long-time friends center on my dating life. It can be uncomfortable because, despite this blog, I am usually a private person. Upon meeting new people, it often comes up quicker than I’d like. Upon going on a date, it complicates some of the conversation.

I also put pressure on myself. In a strange new city, I feel obligated to socialize constantly to meet as many new people as possible. It would help if I were strongly extroverted, but I am only moderately so. 

But, there are many benefits to intentionality. I skip the small talk. I make quick friends. Lots of people find it exciting and want to share their thoughts. I get to show people a sincere part of myself quickly. Some people think I am crazy, but I accept those are not the people for me anyway. 

Regarding dating, I have gone on roughly 25 first dates. It’s the correct number to make progress but not be emotionally exhausted. Twenty of those have been through online dating. Five have been people I met in person or set up. Four of those went on to second dates, but none after that.

Most of the girls are cool people, but for one reason or another, it’s fairly obvious it’s not a good fit even after one date. I happily became friends with several girls afterward. A couple of the dates have been trainwrecks.

I got excited about seven girls. All of them I met in person, which is encouraging for someone who doesn’t like dating apps. However, six of the seven were in relationships, and the other lived far away and was only visiting, which is discouraging for someone who doesn’t like dating apps.

I get discouraged occasionally, but overall, it hasn’t been far off what I expected. I figured finding the right person would take a year or two. I have a unique energy and am looking for something uncommon. Digital nomad daters are quirky bunch in my experience.

Now for the practical parts of the journey. Adult life is still routine. I work, cook, and hit the gym each day. I love my beauty sleep, so I get to bed around 10:30 on weekdays and 11:30 on weekends.

While I am always down for spontaneous social events and adventures, having weekly events like sports teams, book clubs, or improv is nice. Weekly pick-up events are the best because you can go each week but feel no pressure if you have to miss.

Occasionally, I go to pickleball/volleyball courts, bars, and dance halls alone. This can induce social anxiety. However, given the absurdity of my life choices, I can reframe it as a social experiment, so I don’t mind much. I have also met loads of interesting people this way and gotten myself into amusing situations.

Long-term Airbnb rentals are fantastic, especially when the hosts are cool (shout out to Sid and Marie). They are super flexible and only 10%- 15% higher than renting. You get a room, workspace, and access to the kitchen.

Lastly, the mindset is quite different than normal life. 

It’s the opposite of the Camino, where everyone comes for an adventure. I am on an adventure amidst a mass of everyday life. Others aren’t going to bring the same openness and energy. In many ways, it feels like the movie Yes Man.

Planning is undoubtedly a challenge. The intentionality of the journey forces you back to the moment. The journey doesn’t make much sense if you plan too far ahead. You just have to be open to all the opportunities that present themselves from moment to moment.

Early on, I put too much pressure on myself, essentially making social life a second job. But being more forgiving of myself puts me in a better frame of mind.

Overall, I love it. Adventures allow me to be fully myself. My greatest aspiration in life is to participate in meaning. There is nothing like the feeling that you are in the right place, at the right time, and doing the right thing.

From making breakfast in the morning to writing a blog post to deciding which city to move to, my life choices align with my values. What could be better than that?

I’d recommend it to anyone who feels the call to do it and make it their own. 

Life Update: AI Conferences and the family vacation are over. I am moving to Louisville, where my brother lives, for at least a few months. After that, I am considering a long stint in Atlanta or Tampa.