New Here? What Are the Strange Man Trips?
My Travels with Strange Men is a personal travel series about what happens when I say yes to trips with men I barely know (or men I know in only one narrow slice of life) and then discover who they really are, who I really am, and what travel reveals when the normal scripts fall away.
These trips began almost by accident in November 2021, when I invited a man I knew mostly from the internet to share a cabin with me on a cruise. That could have been awkward, stupid, or both. Instead, it became one of the most unexpectedly meaningful travel experiences of my life.
The idea is simple: say yes to traveling with men outside my normal orbit, or at least outside my normal comfort zone, and see what happens when two people are dropped into the pressure cooker of shared meals, shared logistics, long walks, wrong turns, weird conversations, and too much time together. Some of these men were near-strangers. Some were friends, vendors, neighbors, or people I knew in one context but had never really tested in another. The common thread is that travel reveals people quickly, including me.
These stories are not really travel guides, although there is plenty of travel in them. They are stories about friendship, risk, discomfort, status, freedom, business, marriage, aging, self-awareness, and the strange magic that can happen when men spend real time together without the usual scripts. Sometimes the destination is the point. Usually, the person sitting across from me turns out to be the point.
New here? Start here. My Travels with Strange Men is a personal travel series about what happens when I say yes to trips with men I barely know — or men I know in only one narrow slice of life — and then discover who they really are, who I really am, and what travel reveals when the normal scripts fall away.
The stories below are arranged in chronological order, beginning with the impulsive Virgin Voyages cruise that started the whole experiment. You can read them one at a time, jump to the trip that sounds strangest. I will keep adding new Strange Man stories as they are written. To get notified when the next installment is published, sign up for the SCOTTeVEST / Pocket Points newsletter at the bottom of this page.
Choose your Strange Man trip:
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Episode 1: Scott Eddy — Virgin Voyages, Caribbean, November 2021
The trip that accidentally started everything. I invited Scott Eddy, a travel personality I knew mainly through Facebook, to share a cabin on an early Virgin Voyages cruise. What could have been a bizarre mistake became a surprisingly honest friendship accelerant, complete with pandemic-era cruise weirdness, a dolphin-excursion mutiny, and the realization that traveling with a near-stranger can reveal a lot about both people very quickly. -
Episode 2: Glenn Shapiro — Africa and the Seychelles, Early 2022
A safari, the Seychelles, and unfinished emotional business with Africa turned into a deeper lesson in contrast. Glenn’s intensity, confidence, and insistence on sunrise and sunset rituals forced me to slow down, pay attention, and notice some of my own patterns more clearly. The scenery was spectacular, but the real story was what the friction taught me. -
Episode 3: Dirk Dunlap — The Azores, June 2022
This was the first high-stakes Strange Man trip because Dirk was not just a companion; he was an important SCOTTeVEST vendor. In the Azores, we hiked ourselves into questionable situations, made a public weight-loss bet, talked about values, family, faith, business, and life, and turned a vendor relationship into a genuine partnership. This is where the experiment started to feel real. -
Episode 4: Andrew Peterson / Thomas Hawk — Arizona to Palm Springs, November 2022
Andrew was not a stranger, but he was strange in the best and most important way. Calm where I am fast, disciplined where I am impulsive, and brilliant behind a camera, he had already become one of the people who helps keep my life in balance. Our neon-chasing road trip became a story about photography, friendship, money, trust, and the rare person who can document your life while also helping you make better decisions. -
Episode 5: Joe Schultz — Cabo San Lucas, November 16–20, 2023
A trip with my massage therapist sounds like the setup to a joke, which is partly why it worked. Cabo became a study in status, freedom, happiness, and self-consciousness, wrapped in beach walks, scuba disappointment, rooftop four-hand massages, and Joe’s unforgettable rave-floor confidence. Joe had chosen meaning over the obvious version of success, and for a few days in Cabo, I got to see how powerful that choice can be. -
Episode 6: Laird Erman — California, Mid-December 2023
What started as a practical Ferrari pickup trip turned into a roaming California adventure with Laird: Santa Monica, Beverly Hills, canyon roads, Santa Barbara, boat life, Cars and Coffee, and a very Laird-style booze cruise. The contrast was the lesson. I was traveling through California in a dream Ferrari; Laird was living with a fraction of the structure and resources, yet somehow seemed rich in ease, stories, friendships, and the ability to enjoy almost anything. -
Episode 7, Part 1: Andrew Wood's Story of Patagonia, Argentina & Chile, February 2024
What happens when the “strange man” gets to tell his side first? Scott joined Andrew Wood, a British golf publisher and world traveler he had never met in person, for a two-week Patagonia expedition involving shared hotel rooms, endless dirt-road drives, glacier hikes, competitive nonsense, family conversations, and enough close quarters to test whether the Strange Men concept still worked at the edge of the world. This time, Andrew tells the story — and Scott reluctantly lets him. -
Episode 7, Part 2: Patagonia, My Side of the Story
The same Patagonia journey told from my perspective. Andrew Wood remembered glaciers, roads and adventure. I remembered one difficult restaurant conversation that almost derailed the trip—and what revisiting the journey years later taught me about memory, criticism, friendship and why the Strange Men experiment works.
MY TRAVELS WITH STRANGE MEN - Episode One
MY TRAVELS WITH STRANGE MEN - Episode Two: Africa, Friction, and the Discipline of Paying Attention
We were at a dinner party, Glenn and his wife, Vicki, at our house, talking about the world reopening after COVID. He explained that he had a fishing trip planned and several unfilled days beforehand. Safari came up. Africa came up. That sense of now or never hung in the air.
“That sounds like fun,” I said.
And I meant it.
Why Africa Was Different
Safari: Awe Without Illusion
Traveling With Glenn
Seychelles: Beauty and the Discipline of Watching
Alone Again: Integration
What Changed When I Came Home
Why I’ll Keep Saying Yes
MY TRAVELS WITH STRANGE MEN - Episode Three: The Azores, Dirk Dunlap, and Why This One Was Different
This is the one where the “Strange Men” concept stopped being a quirky travel experiment and started feeling… slightly dangerous.
Not dangerous in the “we’re doing illegal things” way.
Dangerous in the much more adult way: the risk of traveling with someone who mattered to my business.
The Pandemic Prologue
It was June 2022. The pandemic was still very much “a thing.” And, if memory serves me correctly, I had tested positive for COVID just a week or two before the trip.
Which created a problem: even if I was no longer contagious, tests could stay positive. The rules were strict, if I tested positive, I would not be allowed to go. I felt great, but I was nervous. The kind of nervous where you’re calm on the outside and just hoping for the best.
I ended up testing at the airport. Negative, I passed. I got on the plane. The trip was on.
And the weird thing is: that initial stress almost helped. Because once you’ve had the “am I even allowed to leave the country?” moment, everything after that feels like a gift.
Who Dirk Was (And Why He Was Chosen)
But he also wasn’t a friend I’d spent real time with in a pressure cooker.
He runs MB Sport, one of our key vendors, and at the time he was relatively new-ish to SCOTTeVEST as a production partner. We’d done business together for several years. He did great work. He was dependable. He had always seemed to have our best interests in mind.
We’d had the normal relationship you have with a good vendor: calls, planning, meetings, maybe dinner once or twice when he visited.
But “vendor you respect” and “guy you can travel with for eight days” are not the same category.
And here’s what made this Episode 3 different from Episodes 1 and 2:
With the first two trips, the escape cord was simple. If the vibe was off, you could split. No meaningful consequences beyond awkwardness.
With Dirk, that wasn’t true.
If we didn’t get along, if this turned into one of those trips where you start fantasizing about separate rental cars and separate lives, the fallout wouldn’t just be personal. It could affect SCOTTeVEST. It could affect our products. It could affect a vendor relationship that mattered.
So yes, I was excited.
And yes, I was also slightly nervous.
Because “Strange Men” is fun when it’s low stakes.
It’s a different game when it’s high stakes.
Why the Azores
I’m going to admit something: I didn’t even know they existed.
The Azores are part of Portugal, an archipelago in the Atlantic that feels like a fantasy version of Earth. Lush, hilly, volcanic, dramatic coastlines, small roads, and the kind of scenery that makes you say, “How is this not more famous?”
We went in June, which is apparently known for rain.
We packed like SCOTTeVEST people pack: thoughtfully, obsessively, and with the quiet belief that we can solve any problem if we have the right gear.
We weren’t sharing a hotel room on this trip, which helped. But we were sharing everything else: rental car, logistics, daily plans, meals, and a whole lot of time together.
And I committed to documenting the trip on Facebook, photos, videos, little recaps, because part of this entire Strange Men series is letting the story unfold in public.
(And yes, it still annoys me that Facebook deleted so many live videos. I have them downloaded elsewhere, unfortunately without the same neat date organization, but if I ever turn Strange Men into a Netflix-style series, those clips will matter.)
The Goal We Didn’t Expect
“Do you have any goals for this week? Anything you want to work on?”
And the hilarious part is that we didn’t even need to say it out loud.
We both looked at each other, two middle-aged men with desk bodies, extra chins, and the quiet recognition that hiking is a great idea until you actually do it.
We both said, almost simultaneously:
“I want to lose 20 pounds.”
So we made a pact.
We would eat well, but we would hike. A lot. And not “cute little walk” hiking. Real hiking.
We turned it into a bet, a public bet that mattered. Not just because of pride. Because accountability between two men who don’t fully know each other yet is a fascinating thing. You don’t want to disappoint yourself… but you really don’t want to lose to the other guy.
What the Azores Felt Like
The people were great. The food, often amazing. The history interesting. The vibe: small, European, quaint, and strangely modern at the same time.
Also: we had better cell service than we deserved.
That fact becomes important later.
The Hiking Wasn’t Hiking
There were many notable hikes, so many that the trip becomes a blur of cliffs, lush valleys, coastline, and sweat.
But two experiences stand out as “Strange Men canon.”
The Ravine / Ocean / “We Might Die” Hike
We ended up down in a ravine and somehow along the ocean in terrain that felt increasingly wrong.
We hadn’t worn enough sunscreen. We hadn’t brought water. And the longer we went, the more obvious it became that we were committed to the bad decision.
At some point the vibe shifted from “adventure” to “math.”
As in: “If this goes sideways, what’s the plan?”
And here’s where it gets real: I was texting Laura while this was happening.
Not dramatic texts. Not “call the authorities.”
More like the modern version of leaving breadcrumbs: “Here’s where we are. Here’s what’s happening. If I stop responding, assume I’m stuck between two sharp rocks having a philosophical conversation with a seagull.”
We genuinely talked about whether we might have to call for help. Helicopter-level help.
And yes, I know that sounds hyperbolic. But that’s what it felt like in the moment. When you’re exhausted and dehydrated and climbing rugged, sharp rock, your brain stops being poetic and starts being practical.
Somehow, we found our way out.
It turned into a four- or five-hour excursion that we did not plan for. When we finally got back, I was proud… and also quietly amazed we hadn’t turned ourselves into a cautionary tale.
The Tunnel That Should Have Been 75 Feet (But Wasn’t)
Someone told us: “Go down this path, you’ll find a little tunnel, walk through it, and you’ll come out to a beautiful lake.”
You hear that and you picture a cute little tunnel. Maybe 25 yards. A quick novelty. An Instagram moment.
What we got instead was a long, dark tunnel with several inches of water, stretching out into what felt like forever, where you can’t see much and your brain starts doing what brains do in the dark:
“Snakes.”
I don’t care if there were snakes. I’m telling you what my brain was doing.
We debated turning back multiple times. We kept going. The tunnel kept going. Here is a video from the middle of the tunnel, not sure if we should keep going or turn back.
We committed. And when we finally came out the other side, there it was: a beautiful lake, like a reward for not panicking.
It was dramatic in the exact way Strange Men trips are dramatic: you choose discomfort, you commit, you question your choices, and then you’re grateful you didn’t quit.
The Relationship Part (The Real Point)
He has four children. I have none.
I’ve had multiple poodles; he has a full family life with a different set of responsibilities and rhythms.
He’s a fairly religious man. I’m more agnostic.
We talked about morals, values, work, life, choices, kids, marriage, and what matters. The kind of conversations men often don’t have when they’re standing at a trade show booth or emailing about production timelines.
And in between those conversations, we were doing something else: We were living together in a confined structure, not a shared room, but a shared reality. Shared plans. Shared decision-making. Shared fatigue. Shared wins.
And that’s where you learn someone.
Not from what they say they value.
From what they do when you’re tired, wrong, lost, or hungry.
The Water, The Cliffs, and the Moment I Didn’t Jump
It was fantastic.
There was also a spot with cliffs and strong currents, one of those places where people jump and it looks amazing, and you realize that if you jump in the wrong place, the ocean will happily teach you consequences.
Dirk jumped in.
I did not.
I’m not ashamed of that. I’m also not proud. It was one of those moments that tells you something about both people. Dirk has a bravery - or a tolerance for risk - that I don’t always share. And I’m okay with that.
The Unexpected Part: SCOTTeVEST Ideas
In a “you have too many hours together, so you end up talking about what you actually care about” way.
We exchanged tons of ideas about clothing, features, improvements, style, and what customers actually want. And many of those ideas have been implemented since then.
That’s a strange side-benefit of Strange Men trips: when you remove the formal setting, creativity loosens up. You stop pitching and start building.
How It Ended
We ended it as something else.
Not identical humans. Not best friends in a Hallmark sense. But bonded. Tested. Proven. The kind of friendship that comes from shared experience instead of shared convenience.
And here’s the kicker: the relationship didn’t end when we got on planes.
Since then, Dirk has visited me and Laura regularly, Sun Valley, Palm Springs, birthdays, events. We’ve continued doing a tremendous amount of business together, and that portion has grown. At this point, he is a true partner in every definition of the word.
People say, “Never do business with friends.”
I get the logic.
But here’s what I’ve learned: if you can do it right, if you share values, communicate, and respect each other, there’s no better way to do business. The trust is real. The incentives align. And the relationship becomes deeper than a transaction.
This trip proved something for me.
The Strange Men experiment works best when the stakes are real and the outcome matters.
Episode 3 was epic.
And yes, Dirk is ten years younger than me. So I’m retiring “two old fat men.” But I’m keeping the lesson.
Middle-aged. Slightly out of shape. Overconfident. Occasionally lost.
Accidental friends.
MY TRAVELS WITH STRANGE MEN - Episode Four: The Strange Man Who Already Knew Me
How I accelerate.
How I chase.
Reposition the car.
He runs across the street.
“Stay there.” Click.
“Now get out.” Click.
Move the car.
It felt like a race against time.
A design language.
A desert confidence.
Americana and asset allocation. Mustang convertibles and measured restraint.
MY TRAVELS WITH STRANGE MEN - Episode Five: Cabo With Joe Schultz
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.
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.
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.
MY TRAVELS WITH STRANGE MEN - Episode Six: California with Laird Erman
The Ferrari
Gallivanting
Enter Laird
The Ferrari Tour
What Laird Appreciates
Santa Barbara
That too deserves a brief explanation.
Years earlier, after getting hit hard during the real estate collapse, Laird took a turn in life that most people would consider either insane or inspiring. Instead of clinging to a more conventional version of success, he bought a boat on a credit card, lived on it in Santa Barbara, and built a life around mobility, skiing, friendship, and a kind of cheerful improvisation. On paper, there are probably many reasons his life should not have looked appealing. In person, it looked pretty damn good.
The time in Santa Barbara was some of the most enjoyable of the whole trip. We wandered the harbor. We drove. We hiked. We went to Cars and Coffee. We spent time in Montecito. We had one of those easy, low-friction runs of days where everything seems to click and no one has to work too hard to make it happen. I do not remember one dramatic conversation or one particular turning point where I suddenly decided to trust him. The truth is simpler than that. He was just easy to trust. Easy to travel with. Easy to be around.
The Booze Cruise
This was classic Laird. Out of thin air, he assembled an eclectic group of people on the boat in Santa Barbara Harbor for an evening cruise that somehow felt both casual and magical. There were drinks, stories, laughter, sunset photos, and the sort of social ease that cannot be faked. I remember standing there thinking that this was exactly the kind of thing I would have loved at twenty, at forty, and now. It had no business being that effortless, and yet it was.
The Contrast
Why It Worked
That California trip began because I had to go deal with the Ferrari. It became one of the highlights of my Strange Man travels because it reminded me that while money can buy access to wonderful things, it cannot guarantee the ability to enjoy them. Laird has that ability in abundance.
MY TRAVELS WITH STRANGE MEN - Episode Seven: The Other Strange Man Tells His Side
Scott's Introduction
Before I write my own version of Patagonia with Andrew Wood, I thought it would be more interesting — and probably more dangerous — to let Andrew go first. This is his version of the trip: two men who barely knew each other, heading to the end of the world, sharing rooms, driving endless roads, hiking, arguing over music, dodging llama-like creatures, and talking about everything you are supposedly not supposed to discuss with a near-stranger. I have resisted the urge to correct every exaggeration, insult, and alleged fact. I have made only light edits for clarity, flow, and public readability, while preserving Andrew’s voice and the spirit of his piece. My version of the same trip, through my eyes, will follow next month.
Andrew Wood's Version
I first met Scott Jordan through his company SCOTTeVEST when I saw an ad on Facebook and bought a vest for my wife’s birthday. I was immediately impressed by the product's quality and versatility and bought my own SCOTTeVEST vest. It really is the perfect piece of kit for a frequent traveler like me.
Sometime later, after seeing more ads for the products, I decided to contact Scott and tell him that I thought his product would be ideal for the golf business, where I have a large reach. We got into an email conversation, and he sent me some product. I wrote some blog posts about my travels in Europe last year, and we started a dialogue. I read his book Pocket Man, which spurred me to write an article about him as a unique entrepreneur for my blog, www.LifeWellLived.expert.
Strange Man Trip
Finally, after going back and forth by email several times sharing ideas, Scott said, “You know, we ought to go on a trip together.”
I said, “Well, I’m going on a trip to Patagonia two weeks from now if you want to come.”
At first, I don’t think he took me seriously, but I assured him I was serious. I was going and had already put together a solid itinerary with a travel company in case he wanted to tag along. Scott had never heard of Patagonia, which, for the record, is a region located at the southern end of South America. It is split between Argentina and Chile and is one of the most remote and unexplored areas in the world.
Scott called the trip “The Strange Man Trip.” I was sure he must be referring to himself. Apparently, this was not the first trip he had been on under these circumstances, and so it became “Strange Man Trip,” version four.
Most people would probably think that two 60-year-old heterosexual guys, who had never met, from opposite ends of the country and very different backgrounds, deciding to go together on a $10,000, two-week trip to the end of the earth and share a room might indeed be quite strange. The fact that neither of us found this situation strange at all should tell you something.
First Meeting in Buenos Aires
And so, after a flurry of emails, texts, and Zoom calls because Scott is a serious over-planner, we met for the first time in Buenos Aires. Buenos Aires was not without some incidents, but I’ll let him fill in the details on that.
Scott was about my height, although it was later proven that I was actually a full inch taller. He was about my weight, although he had just lost a significant amount, beating me by a few pounds on that score. Scott wore a straw hat, which looked good on him; I prefer golf visors. We were both, of course, dressed head to toe in SCOTTeVEST clothing, and I really loved the cargo pants, which I was wearing for the first time. Comfortable, stylish, and, most of all, wonderfully practical for travel.
Amazingly, I found Scott was even more outgoing than I am, which none of my friends believe. Scott says “Hello” to everyone he passes, which works quite well on a lonely hiking trail and not nearly so well on a crowded sidewalk in a city where no one speaks English. During our trip, he stalked at least two tourists wearing SCOTTeVEST clothing. One of them, a New Yorker recognizing him from Shark Tank, was eager to get a picture with him and chat for ages — obviously the first B-grade celebrity he had ever met in person. The other man talked to Scott in nervous chatter, continuing to walk briskly while anxiously looking around for a policeman. “Who is this guy?”
After a hot day in Buenos Aires, marching around town at my usual fast pace, we saw pretty much everything there was to see in a day. At night, we had a wonderful steak meal in the upscale Palermo district and got up early the next morning to fly down to El Calafate, where our real trip to Patagonia would kick off.
Off to Patagonia
When we got to El Calafate, we rented a car and headed off into the desolate yet beautiful landscape toward the town of El Chaltén. The road up there was filled with beautiful lakes, snowcapped mountains, rugged terrain, and llamas — or something that looked like llamas — everywhere. The wind was howling, but I stopped several times to take photographs of the stunning terrain, much to Scott’s chagrin.
Arrive Alive
As I said, Scott is a meticulous planner. He downloads Google Maps, then Apple Maps, takes a paper map from the rental counter, gets hand-drawn directions from the front desk at each hotel, and searches out the concierge to ask for additional options. I prefer to wing it, go with the flow, and head in the general direction of our next stop. After all, there was only one frigging road. Head out of town and take the first left turn. It wasn’t exactly rocket science, just a 200-mile journey straight down Hwy 40 with not a single option presented left or right to go wrong.
I did almost all the driving. This was the call I made early in the trip when, two or three times, I slammed the brakes on from high speed as Scott yelled, “What the fuck?” I pointed several times to a herd of llamas in the middle of the road a hundred yards ahead. The fact that Scott couldn’t see them even after I pointed them out was an early indicator of who should be driving. While I did most of the trip at double the speed limit, Scott was always eager for me to go faster. However, with giant potholes every few yards and llamas crossing the road from every angle, I felt that was fast enough. Half the roads were paved, half were not, and when we dropped off the car, the rental guy was surprised to learn we hadn’t had a single blowout or puncture, thank goodness.
Scott hogged the radio with a bunch of Laura’s playlists, which didn’t seem to make it out of the 70s. Now, to be fair, there’s a lot of good music from the 60s and 70s, but there was a lot of good music from the 80s and 90s, too — not that we ever heard any of it.
First Night Together
Our first night passed without incident despite my snoring and despite what Laura says — or, to put it correctly, what Scott says Laura says.
Laura Dear:
Scott waxed lyrical about what an amazing person you are the entire trip: how the business is built around you, how you keep yourself in great shape, how you are Mensa smart, and much more. All this seems irrefutable. However, Scott also tells me that you tell him he doesn’t snore.
This tells me one of four things:
A: Either you guys don’t sleep in the same building together.
B: Your love for him is so great you’re willing to lie to his face about his snoring problem, which after all is common in just about every middle-aged man.
C: You’re overdue for an appointment with your ear specialist. Since we haven’t met, I obviously don’t want to be rude, but trust me: he SNORES!
D: He is lying about you saying he doesn’t snore?
Anyway, I leave it with you. Just know I have iPhone footage of him THUNDERING out the ZZZ’s which, unlike his footage of me (which he posted), I thought inappropriate to post on Facebook without his permission.
Best,
AW
First Magical Hike
Our first hike was a great success. We did the Laguna Torre hike, a fourteen-mile hike — seven miles out, seven miles back — with absolutely stunning scenery. It was a relatively benign hike to a glacier lake with some of the best pictures I’ve ever taken in my life. When we got back to town, I was ready to do more, but instead Scott took me for a beer, never a hard sell for an Englishman, then went in search of a massage. Meanwhile, I did another smaller hike to get my step count a little higher. In short, I wore him out.
Bragging Rights
The next day, we embarked on a much more strenuous hike, and halfway up the final peak I called it a day and went back to the car for a nap, thus giving Scott bragging rights for the rest of the trip for making it to the top. This even though on every other hike we made, he lagged 300 to 400 yards behind me. Scott, who for the last two decades or more has lived in Sun Valley, Idaho, was like a mountain goat going uphill. Me, having lived in Florida for more than 20 years, was not so good at going uphill. However, on the flat, I took off like the hare while Scott more resembled a wounded snail than a tortoise. I was consistently several hundred yards ahead; however, many people have told me I have a good-looking backside. This is a view Scott got to enjoy for most of the trip. Just saying!
The hotel was a decent four-star but nothing special, but both nights we had excellent meals: one night in a little log cabin reminiscent of a Swiss chalet, another in a fine dining establishment you would not expect to find in a mountain village as small as this was. We ate and drank like Vikings the entire trip and, despite multiple 30,000-step days, did not lose an ounce.
Spot the Gas Station
The next day, the priority was to find a gas station since they are few and far between in Patagonia. We were told there was a gas station on the way out of town just over the bridge, and so we drove out of town, over the bridge, about three or four miles before we decided we must have missed it. We turned around and drove back into town, missing it again. We came out of town over the bridge again and there on the left was something that loosely resembled an abandoned boxcar. Sure enough, cut out from the middle of the boxcar was a single petrol pump, and we filled up.
El Calafate
El Calafate was a vibrant town with plenty of shops and restaurants located on a large bay. Our hotel had a fine view, and we took it easy that night and dined in the hotel after taking a walk along the seafront to get our step count up. The next day, we got up early and embarked on a boat trip to see the glaciers. The water was a sparkling blue in some places and a milky blue in others, but very different from anywhere else I’d ever seen. The glaciers were extremely impressive, and again we got a lot of brilliant photographs.
Chile
The next day, we gassed up and set out on another long journey, this time crossing into Chile. Once again, the scenery was rugged, desolate, and breathtaking all at once. Getting into Chile was a pain in the ass. They had a small wooden hut where you had to line up and show your passport, then go to a different window to show you had permission to take the car out of Argentina, then go to a third window to show your bags. It was a complete joke and wasted an hour of everybody’s time.
Long Drive Conversation
What did Scott and I talk about on these long, desolate journeys? We talked about politics, movies, cars, music, business, marketing, Israel, Laura, poodles, watches, technology, the war in Ukraine, and, inevitably, family. We talked generally about cable news, national politics, and Scott’s complicated relationship with his father and sisters. I have my own family complications, so it was not exactly unfamiliar territory. As I told Scott, you can choose your friends, but you can’t choose your family.
Torres del Paine
The next hotel was a rustic beauty at the foot of a giant mountain in the Glacier National Park. It was our base point for two magnificent days of hiking and a very memorable drive to Grey Lake. The scenery just seemed to keep getting better, and we really lucked out with the weather. For several days, the forecast was for 50 to 80% rain. We literally never saw anything more than one ten-minute shower on the way back from our first hike here. This was a pleasant surprise.
On the first day, we attempted to scale the most difficult trail, but after hiking for only about thirty minutes, the fog rolled in, the wind started blowing, and it briefly snowed. Fortunately, Scott threw in the white flag before I did, so I could blame him for that one. Instead, we went to lower ground and had a beautiful hike along a pristine lake that shimmered a milky blue. That night at dinner, we saw a puma walk past our window — pretty magnificent. The next day, Scott was determined to do the hard hike. I’d already decided I was going to push further down the lake trail. I have no problem walking, but you have to remember I live in Florida. Anything above 100 feet is higher than any point in Florida. Walking straight uphill is not for me. I prefer the mountain passes in Switzerland, where they go every bit as high and higher, but they zigzag up the mountain. Here, they just kind of went straight up. So I had a good time getting in a 14-mile hike around the lake. Scott went up the mountain again for bragging rights, and we met for dinner.
That afternoon, we took the car on a 120-kilometer odyssey on dirt roads to Grey Lake, picking up another entire book of amazing photographs of lakes, mountains, and rugged terrain. The food at the hotel was good, and it was served ranch-style, with only three options each night, which at least kept it simple.
Punta Arenas
Punta Arenas is a city near the tip of Chile’s southernmost region, Patagonia, and was only an overnight stop. Located on the Strait of Magellan, which connects the Atlantic and Pacific oceans, we crossed on a car ferry, which at 58 was a first for Scott. He really must get out more.
Another Long Drive
We were up early for another long drive, this one five hours or so to Rio Grande. When we got there, it was a rather nondescript town. It was also Sunday, the wind was howling, and almost nothing was open. Our hotel was a casino hotel, deader than dead. We walked into the huge restaurant; none of the tables were set, and nobody was in there, but it was open. Scott and I sat down to fish and chips before he announced he didn’t want to stay there, and we should just go to the next town. This was another 200 miles, but it was hard to argue with his logic. There seemed little we would do there except hang out in the hotel room. So off we went, although this time I let Scott do a little bit of driving since I’d already driven for five or six hours. He did fine, just so long as I pointed out the llamas.
Competitive Nonsense and Long-Drive Philosophy
I think we both share the same sense of adventure — the same sense that we should be moving and active and doing things most of the time. I think we shared the same philosophy about entrepreneurism and business. In politics, I like to wind people up whether they’re left or right, because even though I’ve lived in America for 40 years as a resident alien, I’m not eligible to vote, and besides, it only encourages them. Still, despite Scott’s protests to the contrary, I do not feel that he really was a libertarian. We also managed to disagree about age, politics, leadership, and just about anything else two opinionated men can debate while crossing Patagonia. I don’t see why politics even comes into it, but of course it did.
Scott makes way more money than I do, but I’ve had way nicer cars than he’s ever owned. He’s an expert skier. I’m an expert in golf, martial arts, and a decent tennis player, which he tells me he is too. It would be nice to go on a racetrack with him, but I think I’ve got him there. Are we competitive? Hell yes. His watch is worth more, but mine is rarer. Does any of this really matter? No, of course not, but then again, there were a lot of five-hour drives on dirt roads at 120 kilometers an hour.
Did I mention Scott has father issues? Of course, by this point in the trip, I knew enough about him to understand that family, identity, and old wounds were not throwaway subjects. They were part of the long drive conversation, along with everything else. Scott can over-plan, overthink, and occasionally overreact — which, naturally, gave me plenty of material — but I suspect he would say the same about me in his own way.
The End of the World
Ushuaia was a vibrant town of 56,000 people set on the Beagle Channel, surrounded by snowcapped mountains. It was pretty windy and cold, but there were plenty of bars, restaurants, and coffee shops. After wandering around for an hour or so, we picked a place for dinner. I, of course, would have looked at four or five places and picked one. Scott instead asked everyone we met what their favorite restaurant in town was, whether they were local or off the cruise ship from Seattle. We settled on a restaurant the concierge had recommended, and I guarantee you she had never bothered to spend her weekly salary to eat there. Still, in this case, both dinner recommendations he came up with proved to be excellent, if pricey.
This hotel was a proper five-star hotel perched halfway up a mountain overlooking the town with an amazing view and beautiful spa facilities.
Enchanting Final Hike
We took one of the most popular hiking trails in the park, the Coastal Trail. It follows the shoreline of the Beagle Channel and offers stunning views of the sea and the snowcapped mountains of Chile as you walk 5 km through an enchanted forest. It was so beautiful it was almost like a movie set, and I half expected a Hobbit to step out from behind a tree at any moment and offer me a cup of tea.
Most exciting of all, Scott pointed out a golf course on the way back that turned out to be the southernmost golf course in the world. Since I own a golf magazine, World’s Best Golf Destinations, they were happy to host me for free the following day, which was the perfect end to the trip for me.
Was the Strange Man Trip a Success?
Two guys from completely different continents, with totally different backgrounds, who had never met, spent two weeks together in the same hotel room. What could possibly go wrong? The truth is almost nothing. I would rate it as one of my top five trips of my life, and you’re talking to a guy who’s been on a lot of trips in 75 countries and who knows how many millions of miles. Thanks, Scott, for an amazing time, some great products, and a friendship that I am sure will grow.
MY TRAVELS WITH STRANGE MEN - Episode Seven, Part 2: My Side Of The Story
Same trip. Same road. Same table. Different memories.
There is an old saying that there are three sides to every story: your side, my side and the truth. After rereading Andrew Wood’s account of our trip through Patagonia, I have concluded that there may actually be a fourth version: the one you remember several years later, after thousands of photographs have blurred together, the inconveniences have become funny, the landscapes have become almost mythical, and one painful moment has somehow taken up more room in your memory than two otherwise spectacular weeks.
Andrew and I traveled through Patagonia from March 8 through March 23, 2023, driving thousands of miles across Argentina and Chile, sharing hotel rooms, a rental car, hiking trails, meals, conversations, logistical decisions and enough competitive nonsense to fill a separate article. We saw the same glaciers, crossed the same borders, traveled the same dirt roads and stood together in some of the most spectacular places either of us had ever seen. Yet when I recently reread Andrew’s account, I was struck by how differently we remembered the trip.
Andrew remembered Patagonia: the hiking, the llamas—or guanacos, if we are being accurate—the endless roads, the food, the southernmost golf course in the world, and my alleged inability to navigate a region where, according to him, there was generally only one road.
I remembered Andrew and, more specifically, I kept returning to one particular restaurant.
That is not to say I had forgotten Patagonia. I remembered glaciers that seemed the size of cities, water in shades of blue I had never seen before, snowcapped mountains appearing around nearly every turn, and roads stretching so far into the distance that Idaho suddenly seemed crowded. I remembered crossing the Strait of Magellan with our rental car on a ferry, walking through an enchanted forest beside the Beagle Channel, wandering alone through an extraordinary cemetery and completing some of the greatest hikes of my life. I remembered arriving in Ushuaia, genuinely at the end of the world, after tracing an enormous path through the southernmost reaches of Argentina and Chile.
But the fact remained that Andrew remembered Patagonia as one of the five greatest trips of his extremely well-traveled life, while I had allowed one difficult evening to become its emotional bookmark.
That difference in perspective may be the most interesting part of the story.
The Strangest Strange Man Yet
For anyone new to this series, a Strange Man Trip is more or less what it sounds like. I say yes to traveling with a man I barely know—or someone I know only within one narrow context—and then find out what happens when the normal scripts disappear. Shared rooms, long drives, unfamiliar surroundings, physical exhaustion, wrong turns, meals, decisions and too much uninterrupted time together reveal people quickly. They also reveal me quickly, which is often the more uncomfortable part.
If you're new to the series, catch up on all of my Strange Men stories here. For the detailed itinerary, route and day-by-day activities, read Andrew’s version of Patagonia here. Andrew’s account is the better travelogue. This is my version of what happened between the destinations.
The first trip, with Scott Eddy, happened almost by accident. The journeys that followed taught me that there was something unusually valuable about temporarily stepping outside my established life with Laura, the poodles, SCOTTeVEST and the routines I know so well. These trips were never really about assembling a collection of exotic destinations. They were about placing myself in situations where I did not know exactly what would happen, how the man beside me would react or how I would react to him.
Andrew Wood may have been the strangest Strange Man yet because I had truly never met him in person. He was a British author, golf and hospitality consultant, world traveler, SCOTTeVEST customer and affiliate, and online acquaintance who had read my book, Pocket Man, written about me and developed a relationship with me almost entirely through email and occasional video conversations. I knew he was intelligent, charismatic, opinionated, competitive and capable of writing an astonishing number of books. I did not know how he handled stress, whether he was flexible, whether he would irritate me, whether I would irritate him, or whether two outspoken men of approximately the same age could share rooms for more than two weeks without one of us disappearing into the Patagonian wilderness.
On January 31, 2023, Andrew sent me an email with the subject line “Adventure.” He knew I liked road trips and explained that he was organizing a self-driving journey through Patagonia. I had never been there. To be completely honest, I was not entirely certain where Patagonia was or why people spoke about it with such reverence. Within approximately forty-eight hours, however, the trip was booked.
Most people spend more time researching a dishwasher than we spent deciding to travel together through one of the most remote regions on Earth.
Looking back, it was either brave or stupid. The distinction would become clear only after we got home.
Almost Dead Before We Met
The trip nearly ended before Andrew and I had even shaken hands. Andrew was convinced that travelers could sometimes obtain better hotel rates by using a foreign-language version of Expedia. He may have been correct in theory. In practice, it resulted in hotel information printed in another language, a reservation apparently made for the wrong date, and a taxi driver who could not locate where I was supposed to be staying after I arrived in Buenos Aires exhausted and very late at night.
I was carrying significant cash for travel and wearing a new IWC watch I had purchased for the trip and was ridiculously excited about. After the driver circled for what felt like forever, I became frustrated and insisted that he let me out so I could find the hotel myself. I grabbed my bag, stepped onto the street and only then looked closely enough at my surroundings to understand that I had made a spectacularly poor decision.
The area was dark, the drug activity was obvious, and I was standing there advertising that I was an affluent tourist with luggage, valuables and absolutely no idea where I was.
The driver began yelling and holding up his phone: “Unsafe! Unsafe! Unsafe!”
I reluctantly climbed back into the cab, which may have prevented my first trip with Andrew from becoming a very short posthumous story. Eventually, we found the hotel, discovered the reservation problem and obtained what I believe was the last available room. I took an Ambien, went to sleep and prepared to meet the man whose brilliant travel hack had already nearly gotten me mugged.
The next morning, I finally met Andrew and liked him almost immediately. He was highly intelligent, funny, energetic, articulate and at least as outgoing as I was, which is not something either of us encounters often. He was also incapable of walking at a normal pace. We spent hours exploring Buenos Aires on foot, walking somewhere in the vicinity of fourteen miles while talking almost continuously about entrepreneurship, marriage, children, politics, success, disappointment and our relationships with our fathers.
I sometimes joke that these Strange Man trips are a form of therapy. The men are not licensed and, unfortunately for them, are not paid by the hour. Andrew had his own complicated family history, and our willingness to discuss subjects most men carefully avoid allowed us to move almost immediately past the usual introductory conversations. Somewhere during that first day, we stopped talking about what we did and began talking about who we were.
We also discovered that we shared a similar instinct for turning ordinary social encounters into a performance. Whenever someone asked Andrew how he was doing, he would smile and answer, in his British accent, “Legendary.” Whenever someone asked me, I would answer, “Fucking unbelievable.” Neither of us explicitly acknowledged how absurdly similar those responses were. We simply played off one another, two gregarious men independently committed to making even meaningless small talk more entertaining.
By the end of our first day together, I believed we were going to have a remarkable trip. Despite everything that followed, I was right.
Two Men, One Rental Car and Very Different Operating Systems
We flew south, picked up a Toyota Corolla Cross and began our journey into Patagonia. Check out the visual itinerary below. Andrew did most of the driving, partly because he enjoyed it and partly because the car itself held little fascination for me. I love driving Ferraris, BMWs and Alfa Romeos. The Toyota was merely transportation, although by the time we reached Tierra del Fuego it was so thoroughly coated in Patagonian dirt that it appeared to have become part of the landscape.
Our differences as travelers became apparent almost immediately. I prefer information. Andrew prefers faith. I downloaded Google Maps and Apple Maps, gathered paper maps, asked hotel employees for directions, sought restaurant recommendations and wanted to know where we were going before we began going there. Andrew pointed out that there was often only one road and therefore no meaningful opportunity to become lost. I considered that an excellent reason to possess an accurate map of the one road. He considered it further evidence of my neurosis.
The same difference applied to food. Andrew was willing to wander into any restaurant that appeared promising and let fate determine whether the next ninety minutes of his life would be pleasant. I preferred to spend several minutes reading reviews before committing to a meal. His method occasionally produced wonderful surprises. My method produced more consistent results. I learned many things from Andrew on the trip, but trusting random restaurants was not one of them.
Despite these differences, or perhaps because of them, we traveled remarkably well together. Both of us needed to move. Both of us were curious. Both of us enjoyed meeting strangers, asking questions and turning unexpected encounters into stories. We talked constantly during the long drives about business, marketing, cars, watches, technology, marriage, family, Israel, Ukraine, politics, aging and our fathers. Andrew prevented me from filling every empty hour with political podcasts, which was probably healthy. We listened instead to history, including a memorable program about Aaron Burr, and allowed the road to create the kinds of conversations that rarely happen during scheduled calls or dinner-party settings.
One afternoon, while discussing patience, Andrew asked, “Why is patience a virtue? Why can’t hurry the fuck up be a virtue?”
I agreed completely. That one sentence may explain why two men who could each exhaust most normal people found one another so entertaining.
Every night before bed, Andrew also introduced me to one or two short pieces of British comedy. It became a small ritual—something unimportant on its face that I nevertheless came to look forward to. Friendships often develop less through grand declarations than through small repetitions no one intended to become meaningful.
We were also competitive in the most ridiculous ways. Andrew had owned cars he considered better than mine. My watch was more expensive; his was supposedly rarer. He was the golf expert. I was the skier. He moved faster on flat terrain, while years in Sun Valley gave me the advantage when the trail turned steep. None of these comparisons mattered in the slightest, which naturally meant we discussed them constantly.
Business had not followed me to Patagonia in any formal sense, but SCOTTeVEST somehow did. We unexpectedly encountered not one but two customers wearing our products—one on March 13 and another while I was wandering through Punta Arenas five days later.
Finding customers at the far end of South America was surreal, spontaneous and considerably more persuasive than any commercial we could have staged.
The hiking was extraordinary. We completed the Laguna Torre hike together, with Andrew routinely moving several hundred yards ahead of me on the flatter sections. On the hike to Laguna de los Tres, however, the elevation eventually changed the equation. Andrew turned back before the final ascent, while I continued to the viewpoint, earning bragging rights I used frequently and without restraint.
When I eventually returned to the parking area, however, Andrew was nowhere to be found. He had been missing for several hours, I had no idea whether he would be waiting at the car, and I recorded my arrival in real time. The resulting video captures our dynamic better than any retrospective description could: concern, irritation, relief and comedy occupying essentially the same moment.
Fitz Roy illuminated in extraordinary early-morning pink light.
Patagonia kept supplying moments no itinerary could have promised. At dinner in Torres del Paine, a puma casually walked past the restaurant window, turning an already remarkable meal into something that felt faintly unreal.
Several days later, I completed the most meaningful hike of the journey alone: more than thirteen miles, approximately 3,000 feet of climbing and over eight hours to Mirador Base Las Torres. I listened to Phil Knight’s Shoe Dog as I climbed and found myself in a rare state of complete focus. There was no business to manage, no email to answer and no one nearby to impress. There was just the mountain, the audiobook, my own breathing and the decision to keep going.
I became low on water and periodically uncertain whether I was still proceeding in the right direction. The landscape was vast enough that several minutes of uncertainty could feel consequential. You began calculating daylight, distance, temperature and whether your confidence was based on evidence or merely optimism.
Those moments were not flaws in the experience. They were part of what made it real.
The Glaciers and the Restaurant
Several days into the trip, we took a boat through Los Glaciares National Park. The glaciers were almost impossible to comprehend. The water shifted between brilliant turquoise and a milky blue, and the walls of ice seemed less like scenery than living geography.
On the boat, we met two Israeli women and began talking. We had an enjoyable conversation and agreed to meet for dinner later. One of the great benefits of travel is learning how differently people from different countries understand the same history. We discussed one of Israel’s wars, which I had been taught growing up as a relatively straightforward victory. The women had learned a more complicated version, shaped by casualties and human consequences. I found the difference fascinating and pressed the discussion, perhaps more forcefully than necessary. Andrew apparently believed I was being somewhat rude. I believed we were having an interesting conversation. Both observations may have contained some truth.
At dinner in El Calafate, Andrew and I sat on one side of the table and the women sat across from us. By then, we had been hiking, driving, sharing rooms, eating together and talking almost continuously. From my perspective, the trip was going spectacularly well.
Andrew had been drinking that evening; I had not. From my completely sober perspective, he seemed affected by it. Andrew remembers that differently and says he was nowhere near drunk. I do not need to resolve his precise level of intoxication to explain what happened next.
At some point, I excused myself to use the restroom. I initially went downstairs, then discovered that the actual bathroom was only a few feet from our table. I passed behind the group without anyone noticing and went inside. Almost immediately, I heard Andrew begin talking about me.
He complained that I texted him too frequently, constantly tried to coordinate plans, asked where he was, told him where I would be, researched restaurants, overplanned and generally behaved like a pain in the ass. Some of it was true. I did text him often. When two people are sharing rooms, cars, reservations and schedules, I tend to communicate: “I’ll meet you in the lobby.” “Here is a restaurant.” “Where are you?” “I’m going downstairs.” I unquestionably communicated more than Andrew preferred.
The painful part was not discovering that I occasionally irritated him. I have lived with myself for more than sixty years. I am aware that I can be a lot. What hurt was hearing him transform those traits into entertainment for two people we barely knew, exaggerating them in a way that cast him as the relaxed adventurer burdened by his neurotic companion. It seemed less like an honest complaint than an attempt to become more interesting at my expense.
I stood inside the bathroom waiting for the conversation to move on. It did not. Several minutes passed—perhaps five, perhaps ten, although emotional time is notoriously unreliable—and he kept going. Eventually, I had no choice but to return to the table.
The conversation stopped immediately.
I asked what they had been discussing. One of the women, attempting humor in an impossibly awkward moment, said, “You.”
I told them I knew because I had heard every word from the bathroom.
We finished the meal, said goodbye to the women and began walking back to our hotel. I came in hot. For approximately fifteen minutes, I berated Andrew. I told him that I believed we had been having a wonderful time and that if he had a problem with me, he should tell me rather than performing his complaints for strangers. I did not give him much opportunity to respond. My feelings were genuinely hurt.
This was not merely an embarrassing dinner. We still had approximately ten days of travel remaining, much of it sharing rooms in remote areas, and I suddenly did not know whether the man beside me actually wanted to be there. I had always understood intellectually that a Strange Man Trip could go badly. This was the first time the risk stopped being theoretical.
I stayed away from our room for a while and called Laura, trying to make sense of what had happened. Laura was thousands of miles away, probably half asleep, and had limited patience for an international emotional emergency that might appear less significant in the morning. I also contacted one of the women through WhatsApp, who confirmed that the conversation had been uncomfortable and strange.
When I eventually returned to our shared room, Andrew was asleep. He woke when I entered. He was not dramatically apologetic, but he clearly understood that a line had been crossed. I told him, in substance, “Tomorrow morning, we are going to wake up and pretend this never happened. We are never going to discuss it again. But if I sense for a hot minute that you are uncomfortable traveling with me, I am not going to argue, negotiate or stage another confrontation. You will simply discover that I am gone.”
The rental car and most of the remaining reservations were in my name. I had a credit card. I could leave.
Andrew said, “Fair enough.”
The next morning, we woke up and continued the trip. We never mentioned the incident again.
Andrew and I still remember that evening differently. To him, it was a tense few hours I magnified; to me, it was the first real sign that a Strange Man Trip could go sideways.
The Trip That Almost Failed, But Didn't
The surprising truth is that I felt normal the next morning. I did not spend days punishing Andrew, watching him for signs of betrayal or repeatedly reopening the case. I do not hold grudges easily. I had said what I needed to say, he had accepted the boundary and I was ready to move forward. I probably reduced my texting somewhat, but neither of us fundamentally changed who we were.
Looking back, the incident taught me something important about the entire Strange Men experiment. Until then, the risk had largely been part of the entertainment. Of course two men might not get along. Of course one of us might become irritating. Of course a trip could fail. But now something had actually gone wrong, and dealing with it turned out to be simpler than fearing it. We had confronted the edge of the relationship, established where it was and made a mutual decision to continue.
Laura and I almost never fight, and I have sometimes wondered whether that makes our marriage both stronger and, in one narrow sense, weaker. A real disagreement forces people to locate the boundaries of a relationship. It reveals what matters, what can be forgiven and what cannot. Andrew and I found one of those boundaries in El Calafate. He learned that turning my irritating qualities into a public comedy routine would not work. I learned that being hurt did not require me to end the relationship.
The conflict did not deepen our friendship simply because conflict is inherently valuable. It is not. Conflict can destroy a relationship as easily as strengthen one. What mattered was that we dealt with it and then both honored the decision to move forward. One more day became two. Two became three. Before long, we were once again simply Scott and Andrew, driving through Patagonia, debating everything, meeting strangers, competing over nonsense and searching for the next great hike or meal.
Three days after the restaurant, I posted that Andrew and I were “getting along swimmingly.” That was not diplomacy, revisionist history or an attempt to conceal what had happened. It was genuinely how I felt by then.
The pain had been real. The recovery was also real.
By Ushuaia, we were again openly making fun of one another. I posted a video titled “The bitching never stops,” which is either the clearest evidence that the friendship had recovered or proof that neither of us should ever complain about being used as comic material.
The journey continued south through landscapes that somehow became even more spectacular. We crossed into Chile, hiked in Torres del Paine, drove long stretches of dirt road and eventually reached Punta Arenas. There, Andrew and I separated for part of the day, and I wandered into the Cementerio Municipal Sara Braun. I spent hours alone among beautiful landscaping, monuments and mausoleums, absorbing the visible layers of history. My family’s cemetery business was part of my past, but this experience was not really about that. It was about the unexpected pleasure of being alone in an unfamiliar place, following my curiosity without needing to coordinate with anyone.
During the same walk, I encountered a group of young Scouts wearing matching green-and-yellow neckerchiefs and singing in a park with an adult leader. I stopped and recorded them. It was a small, completely unplanned moment, but those are often the ones that remain. Travel is not merely a collection of famous sights. It is also the cemetery you did not know existed, young people singing in a park, a conversation with a stranger or the freedom to turn down a street simply because it looks interesting.
We later drove our rental car onto a ferry and crossed the Strait of Magellan. Andrew found it hilarious that I had never driven a car onto a ferry and declared that I needed to get out more. I found the experience genuinely moving. “The Strait of Magellan” had existed in my mind since school as a distant historical reference. Suddenly I was crossing it in a filthy Toyota with a British man I had first met less than two weeks earlier.
It was one of those moments when geography, history and personal experience suddenly collapse into one another.
By the time we reached Ushuaia, we had traveled through Argentina and Chile, crossed the Strait, driven through Tierra del Fuego and arrived at the Beagle Channel. We stayed at the Arakur, a spectacular hotel above the city with sweeping views and a hot tub overlooking the mountains and water. At home, I use my hot tub every day, sometimes more than once. After nearly two weeks without one, sitting in that water at the bottom of the world felt like returning briefly to civilization.
One of our final hikes followed the Coastal Trail beside the Beagle Channel through a forest so beautiful it seemed constructed for a movie. Andrew wrote that he half expected a Hobbit to emerge and offer him a cup of tea, and that description is exactly right. The trail moved between woods, ocean and snowcapped mountains. At moments, we wondered whether we were lost, another recurring theme of the trip, but we eventually found our way. We met a young Russian woman and walked with her for a time, discussing how the war in Ukraine was being presented and understood inside Russia. Once again, travel placed us inside a conversation we could never have planned.
On our final full day, Andrew went to play golf at what he described as the world’s southernmost course, while I hiked near the hotel and encountered a group of horses. Separating for several hours no longer felt like evidence that anything was wrong. It simply felt natural. We had learned that traveling together did not require doing absolutely everything together.
For our final dinner, I did what Andrew had spent the trip teasing me for doing: I researched the options. He was considering staying at the hotel, but I wanted to go into town. We found a restaurant with a beautiful view and had what may have been the best meal of the journey. We raised our glasses for a photograph and reflected on how extraordinary the entire trip had been.
The incident in El Calafate never came up. It did not need to. We had already answered the question by finishing the journey together.
In my Facebook post that evening, I thanked Andrew for including me on his bucket-list adventure and described it as an amazing ending to an incredible trip. I meant it. A few minutes later, I wrote that whoever became my next Strange Man would have a difficult time topping Andrew because “he was amazing.”
I left Patagonia believing I had made a friend for life and expecting that we would see one another again soon.
Reading Andrew's Version
We have not seen each other in person since Patagonia, although we have remained in contact, sometimes closely and sometimes less so. After the trip, Andrew sent me a draft of his account. Reading it hurt in a way that echoed the restaurant incident. Once again, I believed we had experienced something overwhelmingly positive together, and once again I found myself encountering a catalog of my irritating qualities: the planning, texting, restaurant research, maps, politics, overthinking and occasional overreaction.
Much of it was funny. Much of it was accurate. Taken together, however, it stung.
Andrew did not publish the piece at the time, and we moved forward. Years later, when I began assembling the Strange Men series, I revisited it. With some light editing for privacy, clarity and the protection of people who had not volunteered to become part of the story, we published his version largely as written.
This time, I read it differently.
I finally recognized something that had been difficult to see when the experience was fresh: Andrew’s criticisms existed inside affection, not instead of it. His account makes fun of me relentlessly, but it also describes our conversations, the beauty of the journey, the meals, the hiking, the competition and the friendship that developed between us. He concluded by calling Patagonia one of the five greatest trips of his life, which means something coming from a man who has traveled through seventy-five countries.
His article was not an indictment disguised as humor. It was, in many respects, a love letter disguised as a British roast.
That realization does not make every observation painless or every exaggeration accurate. It does remind me that I cannot control how another person experiences me. I may believe I am being organized while someone else experiences me as controlling. I may believe I am communicating responsibly while someone else experiences me as texting too much. I may believe I am pursuing a fascinating discussion while someone else thinks I am pushing too hard.
The answer is not to abandon who I am or accept every criticism as fact. The answer is to become curious enough to consider what may be true without allowing the delivery to erase the relationship surrounding it.
The Fourth Version
When I first began writing my side of Patagonia, I worried that the restaurant incident would become the whole story because it had occupied so much space in my memory.
Looking back through the photographs, videos and Facebook posts did not prove that I had remembered the pain incorrectly. It restored the pain to its proper proportion.
I did not post about the restaurant while it was happening. It was far too painful and private, and I had no interest in publicly humiliating Andrew while we were still sharing a room and continuing the trip. Its absence from Facebook says nothing about how deeply the evening affected me.
What the Facebook record does reveal is everything else I was feeling at the same time.
I called it the best trip ever. I wrote that it was a thousand times better than I had imagined. I said the journey exceeded my wildest expectations, that I had truly enjoyed Andrew’s company and that my next Strange Man would have difficulty topping him.
There were thousands of photographs of Andrew and me laughing, hiking, eating, driving, resting, meeting strangers, crossing borders and standing together in some of the most beautiful places on Earth.
Those statements and images were not retrospective diplomacy. They were what I believed while I was still there.
The restaurant mattered deeply, but it was never the entire journey.
Perhaps that is the largest lesson. A relationship is not necessarily the worst thing that happened inside it. A trip is not necessarily the moment that hurt the most. Memory sometimes gives pain more authority than joy because pain demands analysis, while joy simply happens.
Andrew remembered the trip in its totality. I had remembered the exception. Revisiting his article, my photographs and my own words from the road allowed me to hold both truths at once.
I also learned that risk is not a flaw in the Strange Man concept. It is the concept. Had I gone to Patagonia with an old friend whose habits, boundaries, moods and weaknesses I already understood, the journey might have been easier. It would also have revealed less.
The unknown creates the tension. The tension creates the honesty. And honesty, when both people are willing to tolerate it, can create a genuine friendship.
Patagonia was absolutely spectacular. The hiking was among the best I have ever experienced. The food was far better than I expected. The driving route was ambitious, beautiful and occasionally ridiculous. Andrew was a capable driver, a formidable walker, an engaging conversationalist, a competitive pain in the ass and an excellent travel companion.
We were more alike than either of us probably wanted to admit: two highly verbal men with strong opinions, a need for constant movement, a tendency to make strangers part of our performance, and stock answers designed to transform ordinary conversations.
Andrew was legendary. I was fucking unbelievable. Together, for more than two weeks, we were both.
Home
Getting home required nearly two full days of travel through Buenos Aires, Panama City, Denver and finally Sun Valley. I made one connection with approximately two minutes to spare and spent the entire journey looking forward to seeing Laura and the poodles.
When I finally arrived, the poodles provided exactly the welcoming party I expected. They did not care about the glaciers, the Strait of Magellan, the hiking statistics, the restaurant incident, the dirty Toyota or whether Andrew believed I texted too much.
They cared that I was home.
That is the other recurring feature of these Strange Man trips. I leave home hoping to discover something about another person and inevitably discover something about myself. Then I return to Laura and the poodles with another story, hopefully a little more self-aware and even more conscious of how fortunate I am to have a home I genuinely miss while exploring the world.
I traveled to Patagonia with a man I had never met in person. I returned with thousands of photographs, one of the greatest adventures of my life, a friendship that had survived its first meaningful test, and a better understanding of how criticism, forgiveness, memory and affection can coexist. The trip almost failed for several tense hours in El Calafate, but it did not—and that is precisely why it belongs in the Strange Men series.