Dispatches - 29 June 2025 - My Final Week and Conversations with Women

What a week it has been. Well, a week and change since my last update. Time is moving fast as my Wayfarer expedition approaches, and I'm not near as ready on the website, Instagram, and YouTube side of things as I wanted to be. Part of that is due to the way the month has gone, and part of it is because I just haven't stayed enough on top of it while being home. That last part is the entire reason I went to Mexico to write my first book. There are simply too many distractions at home.

My trip to Indiana took a hard left before I even landed. My friend's grandmother died while I was in the air, so the whole time I was there, we were focused on the funeral and getting things sorted with family. I had met her grandmother a few times, and she was one of the nicest people on the Earth. I knew it would be hard on my friend when she died, but this came out of the blue. A lot of people turned out for the funeral and the after dinner (like, A LOT), including some of my friend's soldiers from other military reserve units in other states.

I gave them all the space they needed one day by heading into the main part of town to work on my second book for the day. I ended up meeting a girl named Brooke, the bartender at the restaurant where I had lunch. She was cute, confident, with tattoos halfway down her arm, and was wearing a baseball cap and jeans when I met her. I left my number on the receipt, and to my utter surprise she texted me later that night. I've never been a winner with women, so I was ecstatic and asked her out that night. It was a great date. Just a couple of drinks at a bar, but it went really, really well. Even though there were a lot of things in our lives that we diverged on (she's more left and I'm more center right, she's a vegan and I'm not, things like that), we still had a great conversation. Of course I would meet a beautiful, confident woman that I'd like to see again when I was only somewhere for a few days. Welcome to a day in my dating life.

Speaking of women, I also met up with an ex-girlfriend from a long, long time ago. We got to be friends again several years after we split up, but when I left for my second deployment and she got married, we lost touch. She messaged me about a copy of the book, and we ended up talking for about twenty minutes when I took it to her. I was admittedly nervous about the meeting, seeing as I hadn't seen or heard from her in so long, but it was great. We caught up, talked family, shared funny stories, and her youngest child was completely enamoured with my hat. I can't really explain why, but that meeting did a world of good for my self-confidence as I ready myself to head back into the world.

Speaking of women, again, I also talked with a Swedish girl that I met in Tulum. She's just a year or two younger than me, and we're on a similar path. She left her corporate job that was eating her soul to pursue a career as a yoga instructor. She's really cute, and one of the most positive people I've met on the road. When we went to a cenote together in Tulum, she danced a happy dance on the side of the road when we found some fresh mango for about 2 USD. She's back in Sweden now, but leads yoga retreats in Portugal and Spain, and I told her that I was going to look her up if I'm ever in Sweden. She seemed pretty enthusiastic about that prospect.

Shifting gears, starting today, I'm packing and finalising the logistics side of the Wayfarer expedition that starts on Tuesday. Most of my clothes, SCUBA and skydiving gear, firearms, and everything else is packed away in my storage room down the road from my parents' house. I've only one more load of laundry before I pack up the rest. Leaving this time feels different than before. Maybe because this isn't an open ended trip, or maybe it's because I'm going alone from the beginning. I mean, you're never truly alone on the road, but I will be my only constant over the next eighteen months. Just me, my backpack, and my musings (like this one). Fingers crossed that I can turn the musings into a career. That's the ultimate goal.

My next dispatch will be from Spain! I'll be back on the weekly schedule, so stay tuned for updates from the road.