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MY TRAVELS WITH STRANGE MEN - Part V: Cabo With Joe Schultz

Continuing the Strange Men series, I barely had time to come up for air after saying goodbye to Thomas Hawk in Los Angeles before I did something that, even by my standards, qualified as a slightly questionable idea.

I spent one night in Los Angeles, then flew straight to Cabo San Lucas on November 16, 2023, with my massage therapist, Joe Schultz.

Yes, really.

Joe had heard all about these trips because every time I got a massage, I would tell him the stories. Somewhere along the way, while I was planning Cabo, I asked if he wanted to come. He said yes. And just like that, the next Strange Men trip was born.

This one bent my original rule a bit.

The whole Strange Men concept started with the idea of traveling with men I barely knew well, often men with whom I had not even really broken bread before. It was never a rigid legal code, but more a loose framework with one important understanding: if things went sideways, either of us could bail out and move on separately after making a good-faith effort to see whether the chemistry worked. 

With Joe, there was a little more trust and a little more risk. We may have had lunch before, but not much more than that. And unlike some of the other trips, we were sharing a hotel room. My room, no less. Fortunately, I had a pretty strong hunch it would be fine.

It was more than fine. It was fantastic.

Joe was, in his own way, one of the strangest men of all, which is exactly what made him interesting. He came from a background that was oddly familiar to mine in some ways: Jewish, educated, once on a more conventional path, originally in finance. But then he did something few people have the courage to do. He walked away from that world and decided to dedicate himself to becoming the best massage therapist he could possibly be. He had spent months living in India, told stories that hinted at a much more thoughtful and unconventional life than most people ever bother building, and carried himself like someone who had chosen meaning over status and actually meant it.

That intrigued me.

I was not lonely. I travel alone all the time and genuinely enjoy it. But after the success of the earlier Strange Men adventures, I figured: why not keep going? Why not continue the experiment? Joe was available, curious, easy to talk to, and seemed like someone from whom I might actually learn something.

So off we went to Cabo. Check out our first meetup on night one here.

We stayed at ME Cabo, a spectacular, not-so-inexpensive hotel in Cabo San Lucas, right on Medano Beach. Great vibe, great weather, great food, great music, beautiful sunsets, and exactly the sort of place that makes you feel like your life choices, at least for a few days, have been unusually solid. At some point I also had to deal with some bizarre room-charge dispute where someone had billed a bunch of things to our room that were not ours, but even that somehow failed to ruin the mood.

The trip ran through November 20, the day before my birthday, and for a relatively short trip, it packed in a lot.


We did all the touristy nonsense you are supposed to do in Cabo, and some you probably are not. We had our feet cleaned by minnows. We went into one of those pressurized floating air-tank experiences that felt vaguely like something between wellness culture and a science experiment. We ate extremely well. We spent a lot of time in the hot tub. We took photographs, reviewed them, talked endlessly, and walked the beach for hours.

Those walks were probably the real heart of the trip.

Joe and I had the kind of conversations that happen when two men from very different paths discover they are asking similar questions. We talked about relationships, especially my relationship with Laura and why it has worked so well. We talked about success, and more specifically the uncomfortable fact that I was raised in a world where money and status carried enormous weight, while Joe had quite consciously stepped off that track. He had chosen a life that was not nearly as financially rewarding, but was deeply aligned with what actually made him happy. He wanted to help people feel better. He wanted to get really good at something human and intimate and useful. He built a life around that.

And somewhere in those conversations, I found myself admitting something I probably already knew: that while financial success had driven me for much of my life, it had also been overrated in ways I had not fully appreciated until I met men like Joe. People who were not trying to win the obvious game. People who had, in their own way, already won a better one.

That was a meaningful part of the trip.

There was also a less meaningful part involving scuba diving.

Technically, yes, we went scuba diving together. In reality, it involved a two-and-a-half-hour ride each way for what turned out to be a fairly average scuba experience in the middle. Joe was the one pushing for it. We made the best of it. We had fun. But if I’m being honest, it was mostly a wasted day and not the crown jewel of the adventure. Cabo itself, the walks, the conversations, the sillier tourist experiences, and the downtime together were much more memorable.

One especially surreal detail of the trip deserves its own mention. Right next to ME Cabo was an outdoor massage place on the roof, right on the beach, with what felt like about fifty massage beds lined up side by side in the open air. That may be a slight exaggeration, but only slight. Check out my fist impressions here. You could lie there listening to the ocean while two women gave you a four-hand massage simultaneously, all for a sum of money so reasonable it felt almost absurd given how good it was.

Joe and I turned it into something of a ritual, going almost daily and sometimes twice in a single day. I got a real kick out of the fact that Joe, an actual massage therapist and someone who had devoted a meaningful part of his life to mastering that craft, seemed to enjoy receiving massages every bit as much as giving them. And honestly, I couldn’t blame him. A cheap four-hand massage on a rooftop over the beach in Cabo is about as close to euphoric as a person has any right to expect.

And then there was the rave.

This may have been the highlight.

We ended up at a very hip, youth-oriented rave-style party, the kind of place where everyone is curated, deliberate, and extremely aware of how they appear. Before the party even properly got going, before there was really even much of a crowd, Joe went out onto the dance floor alone and started breakdancing.

Or at least what can most generously be described as breakdancing.

Imagine a Saturday Night Live skit. Imagine Jim Belushi trying to impress a room full of attractive, far younger people. Imagine someone moving with complete commitment and absolutely no concern for whether he looked cool, current, or sane. That was Joe. He looked ridiculous. It was glorious.

The bouncer, perhaps sensing that this was not exactly the aesthetic the venue was hoping to cultivate, came over and asked him to stop.

I was delighted.

At first I may have felt a flicker of secondhand embarrassment for him, but that evaporated the moment I realized he had none for himself. And once you see that someone is truly free of self-consciousness, it becomes almost impossible not to admire them. Joe was not performing coolness. He was not trying to fit in. He was not calibrating. He was simply having fun, fully, absurdly, unapologetically.

That stayed with me.

It also captured something essential about the Strange Men series as a whole. These trips were never really about the destination. They were about proximity to people outside my usual orbit. Men with different histories, different philosophies, different ways of moving through the world. Men who, for one reason or another, seemed worth saying yes to.

Joe was absolutely one of those men.


As for SCOTTeVEST, yes, we both wore it, though this was not exactly a trip where the clothing was the star. Beach destinations tend to require fewer pockets than urban adventures. Still, useful summer travel clothing proved useful summer travel clothing. Joe wore SCOTTeVEST pieces including the cabana shirt, performance tee, jogger pants, and shorts. I wore my usual quarter-zip with a SCOTTeVEST logo, and even in a place like Cabo, the utility mattered. Sunscreen, a credit card, a hotel key card, and a phone are the little things that always need a home when you are trying not to carry a bag around all day.

But this was not a SCOTTeVEST commercial.

It was a friendship story. Or at least the story of how an unlikely friendship briefly took shape in a beautiful place, under ridiculous circumstances, with surprisingly meaningful results.

Joe and I did become real friends afterward, and while life eventually complicated that as life tends to do, that is not really the point of this story. The point is that for four days in Cabo, two men from very different backgrounds, with very different definitions of success, managed to meet in the middle and enjoy the hell out of each other’s company.

That is not nothing.

If anything, it is the whole point.

Some men chase status. Some men chase meaning. Some get lucky enough to realize, eventually, that meaning was the better game all along.

And sometimes, if you are open to it, you can learn that from your massage therapist while watching him get politely shut down for breakdancing at a rave in Cabo.

Honestly, that feels like money well spent.