Read My BookMisadventures of a Gringo Dating Abroad

No one said dating would be easy. That couldn’t be more true when you’re dating abroad and don’t speak the language.

This book is first and foremost an account of my personal lived experiences dating and traveling as a now 38-year-old man from the USA (if you say US you might get into an argument you don’t want to have). I’ve lived in Rio for almost three years and I don’t speak Portuguese, and before that I spent several years as a digital nomad. My vocabulary is still “obrigado,” “cerveja,” and a smile that says, “Hello, I’m mostly harmless.”

The first story that comes to mind is my first “date” with a PRO in Medellín. It ended with her berating me in English, in public, for an hour, as if we were married and she’d just found out I was sleeping with her mother. I spent the entire verbal assault trying to get her an Uber home. Looking back, I should have climbed out the bathroom window instead.

There were definitely early warning signs this wasn’t going to be an enjoyable date. Within fifteen minutes of meeting, she accused me of checking out a woman who was clearly on a date with someone else. I explained that the couple was directly in our eye line, since we were sitting side by side facing the restaurant entrance. I eventually talked her down, but it required switching restaurants entirely.

Over dinner she explained that she was a paid escort, which I’d have liked to know before taking her out on a date. I tried to keep dinner pleasant and told her I wasn’t interested in paying for sex. That’s when things went to hell. She took major offense at hearing no, as if I’d decided she wasn’t worth the money, and the date turned into a verbal assault.

I just wanted to finish dinner and go our separate ways. The separate ways part was the hard part. She lived far away and couldn’t afford her own ride home, and her neighborhood was so dangerous that every driver accepted the ride and then canceled once they realized the destination. My solution: drop me at my place first, then her. It certainly extended the awkward situation, but I thought I was being clever. What escalated her onslaught of insults was that I found the entire situation comical. I kept thinking about how I’d retell this story to my friends later.

She was silent the whole ride, which was a huge relief. As the car pulled away from my building, she shouted out the window:

“You need to get your terrible teeth fixed.”

Joke’s on her: I’d already scheduled my Invisalign appointment for the next morning. I’d like to say this was a one-off, but it’s one of many dating mishaps. I’ve reflected on what makes me uniquely prone to these encounters, and I’d like to blame it on being a socially awkward software engineer. In college art class, everyone discovered that I cut my nails down to a dangerous level. My logic was airtight: cut as much as possible, and you have to do it less often. The class was horrified when they saw my hands, and I was mortified.

I’m also a hopeless romantic, and I have been since before I knew what dating was. As a kid I used to wonder how I’d pull off the jacket-over-a-puddle move, where you lay your jacket across a puddle so your date can cross without getting her shoes wet. It seemed like the most chivalrous thing imaginable. Then I’d think: What are you going to do with a wet jacket? Probably leave it, right? Or have some plastic bag situation prepared to quickly collect it after the woman you’re with showers you with affection.

That’s been my love life in one question. Grand gestures, no plan for what comes after.

This isn’t a manual, and I’m not telling you to do what I did. It’s a pile of dating and travel disasters with a few practical lessons mixed in. If a guy with no game, no Portuguese, and a Google Translate survived every one of them, you’ll survive your next first date.

I know what this kind of book can sound like. The passport bro image comes to mind. I’m a gringo in a country where that helps/hurts, and I’m painfully aware of it. Hopefully the stories show that I’m a well-intentioned man looking for companionship in a foreign land. I’ll let you be the judge of that.

I tend to find humor in everything that doesn’t kill me, and that includes the time I was drugged and robbed in Medellín. That one gets its own chapter.

Everything in here happened to me. The names have been changed, and a few details were blurred on purpose. Anyone who shows up as a single letter is a stand-in.

So here’s a glimpse into my dating life that you didn’t ask for.

Since moving abroad, I’ve dated mostly in Colombia and Rio, almost always with no shared language. People often ask why I prefer dating in South America. I usually answer that my primary love language is physical touch, and in my experience the women I’ve met here are openly affectionate from the first date. The signs that she’s into you are also so clear that a socially awkward nerd can detect them. It’s a long glance or someone grabbing your face and kissing you.

No story illustrates this better than my longest relationship abroad. Let me set the scene.

A friend had invited me out for drinks on a random weeknight. I’m not much of a night person or a drinker, but I enjoyed spending time with him, so I agreed. I got hungry and bored at the original place, so I went across the street to have dinner alone at the bar. While I ate, I noticed a group forming. I imagined it was a birthday party. It kept growing, so I sat back and enjoyed one of my favorite hobbies: people watching.

Eventually a stunningly beautiful woman joined the group, and that’s when I really started paying attention. I even remember her outfit: a white top and very blue pants. I couldn’t take my eyes off her. I kept watching the social interactions and thinking about how I might approach her.

Remember, I’m a socially awkward kind of guy. I was certainly not going to walk into a group of thirty people and tell the most beautiful woman what I thought of her. I sat at the bar with a drink for a while, working out a plan. After a minute, I figured it out.

By carefully observing, I noticed one man in the group was very outgoing and friendly. He was always smiling, and everyone greeted him warmly. I watched countless people leave their conversations with him smiling and happy. At first I was a bit jealous. Wouldn’t I love to be that kind of person? I assumed it was his birthday, but the joy seemed like more than a simple birthday could explain.

My idea was simple: buy this guy a drink. He was obviously the life of the party and gifted at bringing people together. (Whenever I try to plan an outing for something special, it’s usually just me and my best friend joking about why the rest of our friends are lame and won’t join.) Buying the girl a drink could come across as too forward, and I had no way of knowing her relationship status or whether she was with anyone in the group. Buying a man a drink seemed like a much safer option.

Executing the plan was slightly more challenging. I don’t speak Portuguese, and I wanted the guy’s preferred drink sent to him, with the bartender telling him it was from me. I think that’s fairly common in America or USA, but not so much in Rio. I struggled to explain what I was doing to the bartender with Google Translate. Eventually I was 80% confident he understood, and I waited patiently as my plan started to unfold.

It was a bold move. To this day, I’ve never randomly bought a drink for a stranger of the same sex. I watched the server deliver it, trying not to stare. The handoff took noticeably longer than I expected, which I assumed meant it was hard to explain. Eventually I saw a gesture in my direction, and I felt relief that my opening move had landed. Now it was time to wait and see what would come of it.

[T], being the incredible human he is, instantly separated from the group to come over and greet me. It was a huge relief that he spoke English. He was extremely charming, well-spoken, and friendly. That’s when I realized I had bought a drink for a gay man. The plan was working, just not on the intended target.

T and I chatted for a bit, and he invited me to join their group, which I did. I was one step closer to meeting her. Now I just needed to integrate into the group and make my move. I talked with people who spoke English and passively observed the group dynamic. When I saw T speaking with her and another woman, I made a point of being introduced. It fell a bit flat. She greeted me warmly but quickly went back to her conversation with her friend. I figured she wasn’t interested and kept my distance.

After a while, I noticed she went to the bathroom. We crossed paths, smiled, and made eye contact in the mirror while washing our hands. I took this to mean she was open to talking, so I simply asked if she spoke English. She said no. I whipped out my phone, and we began exchanging small talk by passing it back and forth, sort of like live-tweeting a date. It made me more comfortable, given my years of online dating, but this was a much more enjoyable version of it.

Some context I only learned later: kissing in public is fairly common in Brazil. If you have a good connection, public displays of affection are encouraged. I jokingly tell first-time visitors it’s the equivalent of a handshake with more bodily fluids. These aren’t pecks; they’re full-on tongue battles. And if you don’t kiss a woman quickly, people often assume you’re gay.

The back-and-forth went on for a while. We joked that everyone thought I was gay because I’d bought T a drink, and I confessed it was a ploy to get an introduction to her. After about thirty minutes of flirting through Google Translate, she asked, seemingly out of nowhere, if I wanted to kiss her. I smiled, said yes of course, and we made out. I’d wanted to the whole time. I was just too into the conversation to think of it.

And yes, if you’re asking yourself, she did eventually become my wife.

Not all the stories I share will be as rosy as meeting my wife. This is one of my favorite horror stories. The setting is Medellín, Colombia, home to Pablo Escobar. There’s certainly no shortage of dating horror stories here. I’ve heard countless stories and even have a few of my own to share. This story doesn’t cover me in glory, but I find it humorous nonetheless.

As with most encounters of this level of horror, it all started with online dating. I’d been talking to this girl for a few weeks. We never met, and the conversation was pretty casual. I even took a trip back to the United States to see family and buy things before returning to Medellín. We stayed in touch while I was away. There were probably several warning signs, but after weeks of talking I wasn’t paying attention to any of them. I’d let my guard down, only to be KO’d in round one, to use a boxing reference.

The day I returned to Medellín, we were chatting. We said we should probably finally meet. I agreed but didn’t expect anything. We had made plans casually a few times that fell through, so I more or less expected the same thing to happen this time. After arriving and getting settled a bit, I chatted her up. We exchanged a few messages. She said she was nearby and agreed to come over for a drink. This is when the alarm bells should have gone off. I was excited to be back in Medellín and didn’t think much of it. It wasn’t my first time in the city. I’d spent a few months there before, and I knew the dangers from stories and firsthand experience.

That night she came over to the hotel where I was staying. We greeted each other. I remember thinking she was nothing like her photos, but again, online dating is a mixed bag. The hotel required guests to show ID and be signed in to get inside, a pretty standard security measure in Medellín. I was still friendly. We chatted for a bit and had a drink.

There was a moment when I sensed things were a bit off. I hadn’t yet finished my drink. I explained to her that I was tired and would probably only have one before needing to go to sleep. It was a subtle cue that I’d like to wrap this up quickly and we could meet another day. She insisted on freshening up my drink, which she made herself. I reluctantly agreed. After a few more minutes of chatting, she excused herself to the bathroom. I sipped my drink and waited for her to be done.

I never witnessed her leaving the bathroom. What I recall is waking up. I immediately noticed she was gone. I sluggishly came to my senses and realized my Apple Watch was missing. I tried to see what time it was, but I couldn’t find my phone. Then it hit me: she had robbed me. I spent the next few moments taking inventory of what was gone.

She decided my very expensive DSLR camera wasn’t worth taking. But my watches, newly purchased MacBook Air, and phones (both my primary and my emergency backup) hadn’t been so lucky. I was pretty perplexed about why she didn’t take the camera. Later I joked that it was a sign I should pick back up the hobby of photography.

I thought I had just been careless and fallen asleep. But when I realized what time it was, I understood I had been KO’d for almost 30 hours. That’s when I realized she must have slipped something into the drink she made. Luckily, I was fine, apart from a bruised ego. I did feel a bit of relief that I hadn’t simply been careless. Then I remembered I knew the dangers and should have known better. She was a PRO, slightly different from the one previously mentioned.

What made the situation even more grim was that after I managed to contact family and access my accounts (way harder than it should be in the digital age, when you have no electronics or phone and everything is multi-factor authentication), I realized she had also gone on a shopping spree. She spent several thousand dollars before credit card fraud protection stopped further transactions. She had even managed to access Remitly, a money-transfer app, and move thousands out of my savings account.

Fortunately, I was able to recover all the money from my accounts, but my possessions are gone. I did file a police report. They had her ID and the location (Find My Phone), but I never heard anything after that. I assume the police decided these items were pretty nice and kept them for themselves. Nothing would surprise me.

Always be careful with your drinks, no matter the environment, especially if you’re around someone new. I’ve even heard stories of people working with bartenders to spike drinks.

While it was much harder to find humor in this situation, I did think it was funny that this had happened basically on Thanksgiving Day. I gave thanks that I hadn’t been physically harmed. I also thought it was ironic that I had planned this trip back stateside to get some neat gadgets, and on day one they were stolen from me. I have a saying now: anytime I’m robbed, I say I’m donating to charity, and the police reports are tax write-offs.

So let’s take a trip down memory lane, back before all this dating abroad was even a thing. I didn’t start traveling internationally until later in life. That being said, the majority of my dating experience is based on my time living in Atlanta, Georgia. Hopeless romantic, Southern gentleman, raised with exposure to women. Could you ask for a more feminine man? Not to mention I’m a double Pisces. I don’t know enough about astrology to know why that matters, but apparently it does. Or so they tell me.

I didn’t date growing up. I was very much into video games and drawing, which consumed a lot of my time alongside normal school activities. I can’t remember what age I was when I had my first actual girlfriend, but it was well after university. It’s kinda wild to think back: online dating didn’t really become a thing for my generation until I was in my teens.

This is a rather embarrassing story, but I’ll tell it anyway. When I say I never had an “actual” girlfriend until after college, I legit mean that. My “relationships” before that were long-distance virtual ones. The first woman I considered myself in L-O-V-E with is someone I never met. I only saw photos and spoke with her on the phone. I’m certain this was a catfish situation before the show had even been imagined. I recall trying to get her to come meet me or even do video chats, with no luck.

We met on the dating app Plenty of Fish. I think it was probably the first one I used. We’d spend countless hours exchanging messages. In those days, I legit had to sit at a desktop and send messages while browsing the web. I think we “dated” for a year or two. All the details are extremely fuzzy at this point, but this was certainly not a typical first-love situation.

Why online worked for me then: I was a nerdy, socially awkward, fat kid. I was well liked, but I never had any “game,” just a friendly personality. My only exposure to women in social settings was at university parties. I wasn’t an amazing pickup artist at bars or clubs. This reminds me of a story from those days.

I had gone to high school with this very beautiful girl, well out of my league at that time. Basically, I considered everyone out of my league. We ended up going to the same college near our hometown. This isn’t a high school sweetheart story, unfortunately. I had a huge crush but would never have bothered to ask her out. I’d see her on campus, and we’d smile and wave. I doubt we exchanged more than ten words our entire time knowing each other. Whenever I saw her approaching our building, I always went well out of my way to hold the door open for her. I even once saw her approaching the building from a distance and did a fat man slow jog so I could get the door for her. She was always very cheerful and kind with her gaze. Apparently that was all I needed for my crush.

One night I was out with some friends at a very trashy college bar. Just cheap drinks, blah music, and a bunch of young wasted university students. You’ll never believe who I saw that night. It was HER. I was just excited to see her in a social setting where I could, in theory, walk up, strike up a conversation, and then confess my love for her.

Needless to say, that didn’t materialize. What did was the first of many funny stories at my expense. I went on with my night without even doing our normal greeting. It started to get pretty late. One of my good friends was buying lots of drinks for us, so that night I got a bit loose. Liquid encouragement was what it was going to take to talk to her. As I was getting ready to leave, I caught her at the bar. I smiled and asked if she’d like a drink. She excitedly accepted. We waited for her drink and just exchanged pleasantries.

I wish I could remember what I even said. I’m certain it had no bearing on what happened next. We got the drinks, I paid, and we went back to the dance floor. I made my best attempt at dancing with her. I noticed a guy looking at us. He didn’t say anything, but the look on his face was, “What is this girl doing with him?” It wasn’t very subtle, so she must have noticed. But instead of thinking that herself, she started making out with me. I was so caught off guard. After a moment, she came to her senses and excused herself. I glanced back at the guy. He was frozen with a shocked look. I shrugged, smiled, and walked away to tell my friends what had happened, leaving him frozen in place.

Fast forward to somewhat later in my dating life. At this point I had a good job and was in shape, so I wasn’t the nerdy version of myself from that story. I was still using online dating to meet 90% of my dates. Just like with my virtual long-distance relationship, it felt very similar. I’d talk to them most days for weeks or months before it materialized into a proper date. Even then, in my experience, a man who’s respectful to women rarely gets a clear sign of interest.

Of the handful of times I actually met a woman in person, one stands out. I was out with my roommate at a “bar” within walking distance of our house. We’d go there somewhat regularly because it was close. I forgot to mention this bar was a strip club. It had a male and a female side, so it wasn’t just a place for sad, lonely men. Women could also enjoy it.

One night I was talking to the woman bartending. I struck up a conversation, and we exchanged contact information. We set up a date for sushi. It was unusual because I rarely go into the real world and meet women. Super excited for the date, I went, and it was seemingly going well. We were talking and laughing. Then she asked me a surprising question. She said, and I quote, “How long have you been dating your boyfriend?” I thought I had misheard her. I said, “Excuse me?” She said, “Yes, the guy you were with the night we met. He’s your boyfriend, right?”

I didn’t know where to begin with my response. One, I was well out of my roommate’s league, the more attractive half of this hypothetical gay couple. If only he were so lucky. Two, we met at a strip club. We met on the female side. I was certainly paying for our meal. While these questions spun around in my head, what I managed to get out was an awkward smile and “Hmm, no.” I actually get the gay comment often, and I find it flattering. I assume it’s because I’m attractive, well dressed, and respectful to women. We both laughed and continued with the conversation.

As we were wrapping up dinner, I paid the check, which I figured was strong evidence against her theory. Then again, I don’t actually know whether gay men pay on dates with women. Somebody should look into that. Anyway, we opened our fortune cookies. Hers was something generic and forgettable. I read mine and couldn’t help laughing out loud. Shit you not, it said, “You should explore your feminine side.” I showed her in disbelief, and we both laughed again.

Surprise, surprise: this gay date didn’t have the intended result. How could something so painfully obvious be confused? Boy Meets Girl, Boy Likes Girl, Boy Asks Girl Out. I know for certain I’ll never have that specific mix-up in Rio.

In Rio, I was trying to build a business around the barracas on the beach. For those who don’t know, barraca is Portuguese for tent, or any constructed stall with a tarp to keep the sun from beaming down on you. I guess. Please don’t take my explanation as fact. Remember, noa fala portuguse.

To drive traffic to the barracas, I “formed” a community of gringos called Carioca Coastal Club and organized beach meetups. If you’ve been to Argentina or Rio, it’s similar to MundoLingo, a language exchange, except the venue is a barraca, not a bar. I brought the entertainment: a beer pong table and a JBL speaker that famously got its own CPF. Foreigners don’t bring a stereo cooler on vacation. I infamously did, on a trip to Cancún.

I hosted several of these, but one stands out. It was a very blah beach day: no theme, no table, just an American football (a novelty in Rio) and my speaker. As always, my friends came, and we slowly accumulated what I fondly refer to as randos.

As host, and out of my own need, I try to bring women into the group. A lot of the gringos who show up want to know where the hot women are, and I smirk every time one of them asks. The women who come tend to be more reserved. Just like a man, I’ll offer my opinion on this: if I were almost naked on a beach, I’d be picky about where I set up shop too.

I also have deeper, better conversations with women. Whenever more than two guys hang out, it slowly turns into a jockeying contest to be the alpha, and I find that very uncomfortable. Most of my closest friends are men, and they’re different in the same way I am. Still, I’ll often do yoga or find any excuse to leave and talk to the closest group of women.

On this particular day, we were throwing the football. I noticed a girl in a brown bikini, in a group sitting close to us. I’ll call her B. I found her attractive, so I made sure to look that way, make eye contact, and smile: Hello, I’m mostly harmless. Come throw the football with us. B was pretty lukewarm. But her friend gave me the signals.

I remember I was trying to get B to throw the ball. She tried halfheartedly, gave up, and went to talk to her friend while I tried to give my Patrick Mahomes impression. I saw them talking. Then I realized the friend, who I now found more attractive, was giving me vibes that she was interested. She eventually came up to me and asked to learn to throw the ball. It was very cute, and I gladly attempted to teach her.

After that, she and her friends joined our group. That’s always the hardest part. It reminds me of beach days with my ex-wife. That’s right, I ended up divorcing my wife from Chapter 1. I’d bring her along, and I enjoyed the beach more because a woman was already in the group. I didn’t need to outsource it.

At some point, I exchanged contact information with B’s friend, the one I “really” taught to throw a ball. I knew all the single men would take their shot at her. I sent her a message: “Nice to meet you. Make sure you choose the right one.” Maybe an hour went by. I was sitting facing away from her, talking to someone. Then suddenly someone interrupted my conversation. She was standing over me, looking down, and said, “Are you toxic?” For a moment I thought, where did that come from? Then I noticed the phone in her hand. She had read my message.

I was able to connect all the dots in almost real time, despite the fact that she had legit interrupted what was sure to be an intriguing conversation. I said, “Yeah, a little bit.” She smirked and started to kiss me. What really made this moment stick in my mind: almost instantly after our kiss, she went back to what she was doing. My friend R rushed over with a huge smile on his face. I don’t remember the exact words, but it was something like, “Dudeeee, right after she kissed you, I started kissing the girl in the brown.” (That was B, the girl I originally fancied.) I smiled, laughed, and did my little shrug.

What made it even better: I enjoyed the day a little too much. I don’t normally drink much. It’s Rio; it’s dangerous enough without being the sloppy drunk trying to get home. I also normally take everything I own to the beach. I guess being drugged and robbed taught me that I can lose it all and still be okay.

I woke up the next day and typed in the group chat I use to organize all the beach meetups, over two hundred people, thanking everyone for the nice time and saying that I was so drunk I didn’t even remember getting home. Less than a minute later, my best friend C responded: “All I remember is you making out with the hottest Argentine girl.” We joked afterward that we’re in so many groups together that he responded as if it were a conversation between the two of us. It was slightly more than the two of us.

I know what all this is starting to sound like: dating advice from a pickup artist. I want to make clear that’s not the case. This is the only time I’m going to address my opinion on the subject of meeting or “picking up” women. I attribute any appearance of success to the fact that I’m very comfortable in my own skin.

The only advice I want to provide in this book is this:

MEN, you need to fix YOU before there can ever be a YOU + 1.

If you’re reading and interested in that, I’m certain there are plenty of other books out there for you.

I debated whether to include this part of my life in this book, but I’m bipolar. I know you’re thinking, what does that have to do with anything? Guess I lied twice. The intro said this was just a random dump of dating stories. But what I’ve come to realize is it’s more about me expressing my life in a humorous way. Who doesn’t love a rom com.

Does being bipolar affect dating? In a single word: YES. But that also depends on your definition of hinder and dating. Brazilian dating terminology would require an entire book to explain. I’m going to step over that huge elephant in the room and focus on the ways it hinders me [Vincent].

The most obvious one is when there are major depressive episodes. There are times when I’ll sleep for multiple days in a row only waking to do a small bit of life admin before sleeping again. Surprisingly, the women you’re “dating” aren’t fond of you disappearing for any length of time. I’m sure I don’t need to explain this to anyone who’s married.

Also, bipolar isn’t something people usually include in their dating profile. But I often post about it. I even had it in my IG bio for a while. Might not want to go around talking about it on a first date as well. The taboo of this subject is so strong that it can drive away close friends.

In the next chapter I’ll discuss the countless other reasons why this would be a huge RED FLAG in dating. But the important bit is that I work every day to overcome these personal limitations in my own life, independent from anyone else.

My diagnosis didn’t come until later in life. I had just ended my first very serious relationship in Los Angeles. I think the separation affected me much more than I realized at the time. I started what is referred to as a manic episode ramp-up: multiple days of escalating, chaotic behavior.

It eventually got so bad that I needed to admit myself to the psych hospital. This experience was extremely traumatic. Not for the reasons you’d think. I have a lot of strong opinions about mental health (that’s why I have the butterfly tattoo on the back of my neck), but I won’t share them here. What I will say is that the system isn’t designed to help. It’s set up for people with the means to pay indefinitely for meds. There’s also very little consideration for the problems affecting the individual person. (don’t like the sound of this)

At this point I’ve surely lost you. When did this change from funny dating mishap stories from a misinformed gringo? And you’re right, back to regular scheduled programming.

One day at a Carioca Coastal Club meetup, I was really enjoying the SUN (I’ll use this as code for what we in the industry call being cross-faded). Cross-faded is when you’re high and drunk at the same time. It’s an interesting dynamic to hold in public. I normally end up making a fool of myself when I’m like this.

This day was chill. A few of the regulars showed up. What was special about this particular day is that a regular brought a very beautiful friend, [M], with her. I was curious to meet this new person. While I’m not particularly close to the friend who brought her, I’d consider us friends. I wasn’t going to hit on [M] and make the dynamic awkward.

I thought I greeted her normally, per usual. My memory is extremely foggy here, so take all this as a cross-faded person’s account. I asked her to be our DJ for the day. I listen to endless amounts of my own music, and it’s nice when someone shares the DJ duties so I can relax. Hosting is a full time job and doesn’t pay well. I was extremely reeeeelaxed this day.

A few weeks later, I invited [M] on a date after confirming with my friend that she’d be interested. On the date, [M] told me my memory of us meeting didn’t go the way I had thought. I said, “Ohhhh, I was cross-faded that day. What embarrassing thing did I do?” I remembered falling, but it was a difficult position to get up from, sitting in the sand. (Not even with all my years of yoga would I have been able to pull it off easily, sober.) She told me that at some point I’d kissed her shoulder. She asked our mutual friend, “…What’s wrong with him?”

I couldn’t help but laugh at myself. I vaguely remember doing this, but I thought it was a quick peck. In her account, it was a full-on Brazilian make-out with her shoulder. Apparently Rio life has rubbed off on me too much, thinking it’s okay to make out with a shoulder.

Needless to say I was pretty embarrassed on that date. Oddly enough, we discovered we are neighbors, and now my neighbors know me as Shoulder Kiss Guy.

I haven’t told you this yet: I’ve had three major manic episodes. Two happened while I lived in LA, and one happened abroad, in Japan. They were all uniquely terrible, but Japan is the one that still resonates with my family and close friends, and it’s by far the worst.

Speaking Portuguese seems like child’s play compared to Japanese, and I think that’s part of what made this episode so much more frightening. I wasn’t just abroad. I was about as far from home as possible, in a place that’s the opposite of the USA in almost every way.

If you’ve made it this far, here’s the part I don’t tell on first dates.

All of my episodes have had one symptom in common: I become extremely paranoid. In Japan, I became convinced that the college friends who’d come on the trip with me were being controlled by Japanese gangsters. I stopped contacting anyone back home because I was afraid the mob would do something terrible to them.

I don’t think I’ve ever told anyone this next part. I had also convinced myself that a gang in Brazil would kidnap my girlfriend who lived in Rio if I tried to contact her.

I can’t recall how many days I was in that state. I think it was a week or more. I remember carrying everything I owned around Tokyo, sleeping outside for multiple days. I was so paranoid I couldn’t even use my credit cards to get a room, because I thought they’d take all my money, or worse.

I only got home when I trusted one of my friends enough to reach out. I was still extremely paranoid, but I put the paranoia aside and trusted him to help in this difficult situation. In some ways, he saved my life. Unfortunately, we aren’t even friends anymore, and that deeply saddens me.

I also lost the relationship with the girl I was dating at the time. She is the one I considered my first girlfriend abroad, and she ghosted and blocked me. Thinking back, I took that harder than the entire episode. I was having one of the worst experiences of my life, and I was still worried about her safety and well-being, even though I was the one in danger. I stayed silent to protect her. She heard silence and left.

It’s very easy to explain a blackout-drunk night socially. There’s a clear reason: you drank too much and can’t remember what you did. Maybe it gets you nicknamed Shoulder Kiss Guy, or you get into a fight with a family member. The next day you sober up, acknowledge what happened, and try to move on with whatever relationships it affected.

A manic episode doesn’t work that way, in my experience. Most people probably think you’re fucking nuts, and that you belong in a hospital. The ones who don’t think that take a long time to shed the trauma of seeing you in that state. I understand this. My mother and sister took it extremely hard.

I’ve told this story more times than I can count. It cost me a relationship, a friendship, and a lot of money. But I don’t let it dictate how I live my life. It also taught me one thing: even your chosen family will struggle with an extreme manic episode. That goes for dating and for having a partner.

I’m perfectly okay talking to anyone about this experience, but it needs to happen in person.

I want to thank everyone who helped and thought of me during that time. I couldn’t appreciate it then. Sometimes at your lowest point, you feel other people’s love the strongest. Extra gratitude goes to my family and my close college friends.

I hope my future wife reads this book and truly understands what my life was like before she came into it.

Before actually living abroad I tested the waters with numerous international trips. My first love was Ecuador. One of my best friends is Ecuadorian, and The Carrollton Crew organized a trip to see his country. There’s probably multiple chapters worth of content on these Guys Trips.

These trips sparked something in my soul that I had always felt was missing. So many new experiences. When I was young and poor, I never could understand why people would spend so much money “traveling.” I’d think… you spend how many thousands of dollars? What do you have to show for it? A few pictures of yourself in front of things I can easily google and see for free? Count me out.

One of the most unique dates I’ve been on happened in Edinburgh during what’s called the Fringe Festival. One of my besties [a] lovessssss this festival and trip. Sometimes, months later, he’s already planning next year’s trip. His enthusiasm about it is what makes me truly enjoy going. He even convinced me to visit Munich in Germany. I think I bitched the entire time about how much I didn’t want to be there.

These trips slowly became how I anchored my whole life. When was the next Guys Trip abroad? After the Japan trip these haven’t happened. I’m hoping that the next one will be everyone coming out to visit my new home in Rio. Cough cough, fellas… March 17, 2027, seems like a good time to visit. Just saying.

Those trips are the reason I said yes to things I never would have at home, like getting pulled on stage in front of strangers. South America rubbed off on me in other ways, too. I’d picked up a new hobby: petty theft. Nothing serious, just the occasional apple or something small I could easily have paid for. Don’t worry, I don’t still do this… much.

The Fringe Festival is one of the biggest comedy festivals in the world. Lots of comedians go there to test out their material or make a name for themselves. It lasts several weeks. This date was memorable because it was done on stage as a part of the comedy show called Never Date a Comedian. If this book ever gets me into comedy maybe one year I can be one of the comedians you wouldn’t want to date.

After all my other dating experiences this wasn’t as scary as you’d imagine. They pulled people from the crowd (most of whom had been prearranged) to come on stage. They asked some questions about you, made a few jokes, and introduced the comedians you’d be interviewing for a date.

When it was my turn, they pulled me on stage, my friends cheering the loudest. I used to have stage fright, but I was surprisingly comfortable being on the stage. It did help that I was sitting and the host was doing most of the question asking. I remember thinking, I hope one of them is pretty. Another opinion you didn’t ask for: I rarely find female comedians funny. The ones who are aren’t what I’d consider my dream match.

I don’t consider myself to have a type, per se, but there are certain things I value more than others. A friend I was getting to know once asked, “…what’s your type, physically?” In mixed company I answer, “I can find many things beautiful in a woman. What does it for me is what she’s most proud of about herself. That’s usually where my attention goes.” If they press harder, I simply say bunda now.

The nerves didn’t really kick in until they started bringing out the comedians. One by one they came out. I would smile and nod in approval. I suddenly became very aware that my expressions were under a microscope, not only from them but from the audience too, who were now focusing on how I interacted with them.

Something you can’t exactly see when reading this is that I have an extremely expressive face. It gets me into a lotta trouble trying to hide my emotions in real time. There are numerous photos of me passively judging someone with my eyes. I quickly reminded myself of this fact. I started to feel a bit more nervous than at the start.

Thankfully, to my relief, the last comedian was someone I fancied. I thought she was cute, but not my usual type.

Each comedian started with a greeting/introduction to be funny and start a conversation. Each woman said her bit, I engaged and faked as much interest as I could, and then the next would go. The last one to go was my preferred choice. I won’t say exactly how she chose to introduce herself, but she invited me on a tandem bike ride as a getaway from a crime.

As an opener, she couldn’t have chosen a better one. Given my new hobby, it triggered an almost instant response to her question: “…Are you down?”

Without skipping a beat, I simply asked, “Front or back?” The crowd let out a huge laugh. Even the hosts, who were comedians themselves, couldn’t help but laugh. I felt like I had come a long way from the days I put my foot in my mouth.

After the show we went on a very pleasant date. At some point I’ll dig up the photo of the two of us, me overly cheesing with my fucked up teeth.

Besides Chapter 1, none of the dating stories so far amounted to a serious, committed relationship. Some were a one-off kiss out of nowhere. Others were casual flings. They’re entertaining to recap, but they didn’t exactly make me feel cared for or SEEN.

I’d like to offer the readers a little hope, if you want it. Life doesn’t have to be an endless game of Firsts (first date, first kiss, first argument). I wasn’t sure how I’d write about this one, but I’ve come to find out the person in question has blocked me, so I can basically say whatever I want about her. What I want to say is that she’s great.

That’s the interesting part: we never had a fight or a serious disagreement. For whatever reason, it just didn’t work out. It was confusing to hear, at the time, that she wanted to end things. Deep down, I could also feel something was missing. The spark wasn’t there, but I was willing to try different fire-starting techniques, to use a bad metaphor.

Let’s call her [M]. I had finally found someone who not only spoke English but was in fact an English teacher. It was the first time I could see a legit future with someone since ending things with my ex-wife.

I’ll quickly share how we met, because it was humorous to me on a lot of levels. I met [M] on a dating app. We exchanged a few messages in Portuguese, obviously with me using Google Translate. Once I noticed we had a decent conversation going, I asked her to go off the app, basically to talk on social media or exchange WhatsApp. She responded that she’d rather keep talking on the app.

I gave it my best attempt at humor in Portuguese and said something like, “I’ll make an exception for you and keep using the app.” Suddenly the conversation went cold. I didn’t think much of it. This happens often when online dating. You can get blocked or unmatched at any time, for any reason. It really starts to feel like white noise.

Fast forward a week or two. I open the app and whose message do I see? [M] had sent me a message saying hello, she’d just seen me walking down the street. In English. That seemed odd. Why would someone who “ghosted” me reach out in English, and also know what I look like well enough from photos to notice me on the street?

We exchanged some messages and agreed to grab some food that day since we were both free. On the date, I asked how she even knew it was me. She said she’d heard the News Stand Guy greet me by name. It was near my house, so I went there often. Then the topic of why she originally didn’t keep the conversation going came up. She said the way my message about making an exception for her came off in Portuguese seemed rude. I was honestly shocked, but I didn’t linger on it. Internally, I was thinking: thank God she didn’t know me as Shoulder Kiss Guy. That would have been much easier to interpret as rude, and that one happened in person. Fair enough on the translation, though. Google Translate and I have made enemies before.

This story will always stick with me because not speaking the same language wasn’t the problem here. It was that we couldn’t fully express ourselves with one another. We lasted about eight weeks.

This was fairly recent. I’m almost 40 at the time of writing, and I’m very much at the stage where I want a serious partner. I don’t want to speak negatively about dating in Rio. I love this place with all my heart. But it does offer some very interesting hurdles. I consider Rio the Las Vegas of South America. It doesn’t only bring party-loving tourists from all over Brazil. It brings them from the entire world.

Like I said, I’m not a big partier. I know most of these stories have included alcohol, but I’m actually a pretty health-conscious person. Alcohol is a depressant, so it can trigger depressive episodes. Don’t get me wrong, I let my hair down every now and then. It’s by no means the norm.

Here’s why I think dating in Rio is difficult for me: I’m someone who loves a sunrise because I woke up for it, versus someone who’s been out all night and happens to see it. There’s a “what happens in Rio stays in Rio” mindset. Most expats living here don’t think like this. Sure, it would be fun to live like it’s a constant party. But who’s gonna pay the bills?

I said early on that I’m divorced. The most obvious reason we’re not together is that I cheated on her. That’s the danger of all this: a seemingly innocent day out can end with you kissing someone you shouldn’t. But it’s a lot more nuanced than that. I’d like to take a minute to describe why that relationship ended. You already know the story of how we met.

In the beginning, things were casual. After a few weeks of seeing each other, I told her I was enjoying it but couldn’t see it becoming exclusive until one of us learned the other’s language. Props to her, she’s basically fluent, while I’m still struggling to get out the simplest of Portuguese words.

Over time we kept getting closer, and I started to change my opinion. She was improving every day, too. After about two years, we decided to make it exclusive. That was the beginning of the end. While we’d been casual for almost two years during my Digital Nomad phase, we seemed to have amazing communication. Sure, we had our issues, but we always found our way back to each other.

Looking back, the two relationships are mirror images. With my ex-wife, I could barely speak her language and we still communicated amazingly, until we got serious. With [M], we shared a language, but I still didn’t feel like we truly understood each other.

I genuinely wish her the best. The Dutch have an expression for moments like this: zand erover (sand over it). Luckily, I live in Rio. We have plenty of sand.

Remember when I told you I’m not much of a nighttime partier? I’ve known that about myself for a long time, and it still didn’t stop me from trying. I think as men we’re conditioned to believe the best place to meet women is a night out drinking with the boys. That might work for some people. It never worked for me. Most of my attempts ended with my friends and me trading wild stories about what happened the night before, almost always without any women.

Two besties were with me on most of these nights, [M] and [H]. [M] is my Ecuadorian friend. [H] and I share a birthday, a year apart, and I’m the oldest. I consider both of them my brothers. I’ve lived with both, and they’re my ride-or-die homies. I’ll tell one story about [M] and leave [H]’s to [H], because they’re better told by him. They both deserve a place in this book.

[M] is one of my oldest friends. We went to college together, but we didn’t get really close until we moved in together after uni. We’ve had countless adventures, but the ones that make me smile most are from our first trip to Ecuador.

As I mentioned earlier, that was one of the first group trips with the Carrollton Crew. Besides the countless wild nights out, what made it memorable was getting to see the country my best friend is from. We met his family. His cousin [F] was basically our tour guide the whole trip, taking us places most tourists never go. He even acted as my personal flirting translator when [M] got tired of his translating duties.

I want to take a moment to say how grateful I am to have [M] as a friend. He has always been loyal, even at my lowest moment. After my manic episode in Japan, our relationship changed. We aren’t close right now, and we haven’t spoken in almost a year. [M], I’m sending you this chapter hoping we can repair things. I honestly don’t know everything you’re upset about. When we fell out, I blocked you because I didn’t want to hear it. I’m sorry for that, and for whatever part I played. I’d like to hear it now. The way I see it, brothers fight, and they always find their way back to each other. Okay, writing that line made me feel a little gay. (I say it that way because men always joke like that when we express love for another man.) It’s definitely a defense mechanism, but I digress.

Anyyyy who, one night in Ecuador we went out drinking in Montañita, a small beach town. If you haven’t been, I highly recommend it. We were all out trying to meet women. Like I said, that usually meant hanging out with each other and striking out with anyone we had the courage to approach. Ecuador is also where I fell in love with South American women. I forget the details, but I had [M] chat up a girl I thought was interested. I hadn’t exchanged a single word with her, and she was veeeery interested. I thought, wow, that was too easy. We kept dancing together. Later we saw a woman I’d talked to earlier that day. I said hello and carried on with the girl I’d met that night. Some time passed, and my friends were talking with the other girl and her friends. We were basically one big group by then. Forgive me for not remembering the exact point of escalation, but the two girls started fighting over me. I couldn’t believe it. How many nights had we gone out with no prospects, and here were two beautiful women fighting over who got to take me home? I remember stepping out of the situation and telling my friends, “To the victor go the spoils.” I took home the winner.

A quick aside to thank my friend [H]. One memory will always stick with me. After my Japan episode, [H] and I were supposed to be roommates in Medellín. I was afraid the stories our mutual friends told about how bad it had been would change his mind. [H]’s heart is huge. I often say he’s nicer than me, and that’s coming from someone who once got a sex worker a ride home after she verbally assaulted me.

When we talked about the arrangement, I fully expected him to back out. He basically said he wasn’t worried and that shit happens. His seeming indifference came as a shock. I’ll always remember that conversation. I’ve never felt such certain acceptance and comfort.

Okay, that’s enough lovey-dovey feelings. I’ll end the chapter on this note: if you ever get the chance to hang out with [H] and me on our birthdays, be sure to ask him about the girl who turned lesbian hours after meeting him.

This cliché phrase is how young me always thought love worked. You see someone, you like them, and that’s the end of the journey. Married, with the white picket fence. Boy, was I wrong.

Per usual, this phrase reminds me of a time I couldn’t see the girl I asked out at all. Let me explain. While I was living in Atlanta, I was a big runner. I’d run at least a mile a day, if not more, but never any long distances over 10K.

One day I went for my run on the BeltLine, where most people in my Atlanta neighborhood would go to run. It’s basically the orla in Rio, but without a beach. This day, I forget what happened; my memory is a little shaky on specific details. I think I decided to go for a run without my contact lenses. I couldn’t be bothered to put them in. I knew where I was going, so it wouldn’t be that big a deal.

For those who don’t know, I’m extremely blind. I can only see clearly to about the fingertips of my outstretched arm. I’d never attempt a no-contacts run at night or somewhere new, because it could be extremely dangerous. When I run, I like music, and not just in my headphones.

I’d carry my UE Boom portable Bluetooth speaker. It had several useful benefits. I could sing while running, and the music would mostly drown out my terrible voice. It also warned people with their backs to me that I was approaching, and they’d often shift to let me pass. This day, it surprised me by helping me meet a woman, something I never imagined happening, since I was basically blind.

I had never met anyone in my countless hours running on the BeltLine. I was focused on the run, not on meeting someone. Plus, being super red-faced and sweaty probably isn’t the best first impression. While I was running, I passed a woman, also running, who I imagine was attractive. I probably didn’t even attempt eye contact. What’s the point? I can’t see her eyes anyway. I remember the color of her clothes and her hair.

We passed each other and I didn’t think anything of it. Since I was running with music, people often look in my direction, so that wasn’t any indication she was interested. It’s hazy, but at some point we ended up running in the same direction at the same pace. I think I overtook her at some point. She was fast, so I remember it taking a lot of effort.

After passing her, I was a little tired and slowed my pace. I noticed she had also slowed down. If she had kept her pace, she would have passed me again quickly. I kept running, aware she was behind me, watching. I thought, mmmm, I have no idea what she looks like. I could only see well enough to make out fuzzy shapes.

Some time went by and she was still behind me. I’d recovered some energy from overtaking her, but I decided to walk so I could talk to her as she passed. This time when our paths crossed, I asked her if she liked the music I was playing. I was the DJ for our run. She smiled, I think. I couldn’t see her face well. She said yes, we talked for a minute, and we exchanged numbers.

When we were about to part ways, I confessed that I was running blind (literally). She laughed and said, “Huh?” I explained the contacts and my terrible vision. I might have said, “See you later, beautiful,” while gesturing to my eyes.

When my ex-wife and I separated, I took it very hard. People deal with grief in interesting ways. I took the drink-the-pain-away approach at first. I didn’t want a logical mind that tried to explain why things with the love of my life didn’t work out.

Remember I told you Rio is like Vegas. That makes it a great place for a rebound but a terrible place to actually lick your wounds. Armed with only a broken heart and a healthy drinking problem, I went headfirst into dating again.

I’m not proud of this, but it didn’t take long for me to “move” on. One night in particular, I was out drinking with my friend, discussing the breakup and how it was making me feel. We started talking with a group. I found one woman attractive. He made the introduction and began doing the job of being my translator for my flirting.

I don’t remember what was said, but she agreed to come back with me. I warned her my ex’s stuff was still in the apartment. She didn’t seem bothered by that. It’s really ruthless out here in Rio.

We started being intimate, and that’s when I realized a biggggg problem.

She was very built, almost a bodybuilder physique. I’d never been with someone more muscular than me. Apparently there’s an interesting thing that happens when women use testosterone to build muscle. I was now looking at one of its side effects, and I had a mini panic attack. Had I just taken a trans woman home? How did I not know? Upon a more thorough investigation, I confirmed she was indeed a woman, but I couldn’t shake the original shock. We didn’t hook up that night.

The next morning I messaged the friend who introduced us and told him what had happened. He laughed and said she had mentioned all of it to him while they were talking: the testosterone and what it does. Of course, this flew over my head at the time.

Not having actually finished my “mission,” I went back out on the hunt. This time at the beach. I was a little scared. I thought to myself the best way to avoid bringing home someone questionable is to see them in their bikini. Surprisingly, this is also harder than you’d imagine, since your senses are impaired.

That day I spent doing my favorite things, relaxing on the beach. But today I was exceptionally lonely and getting drunker than I usually would. I was buying beers from the barraca ten at a time. This was before I realized you could simply return the ones you didn’t drink. Once I felt myself getting a bit too drunk to be in public, I looked for someone to give my beers to. Unfortunately, I had just ordered ten, and I really shouldn’t have kept drinking, especially alone. I looked around and saw a beautiful woman alone. I had seen her before but couldn’t be bothered to Google Translate-flirt with anyone that day.

I approached her with the giant bucket of Heineken. I asked if she spoke English, and to my surprise she responded in perfect English. I lit up. I had found my drinking partner. At this point my goal was only to give her the drinks and leave. I said, “Want ten beers!?” She said yes and laughed. I put the bucket down, then went to collect my things to leave.

I fully intended to just leave, but it was still nice out and I wasn’t done enjoying the beach. I went back with my things to ask if I could join her. She said sure, almost surprised I asked. Who drops off ten beers and leaves? It’s the worst pickup approach ever.

My fondest memory of this interaction was what happened next. We talked. I explained everything about my breakup. She was very understanding and warm. Then she asked to read my palm. I thought it was cute. What information could she get out of me?

She began to read my palm, saying some generic stuff. Then she uttered something that still makes me tear up to this day. She said, “I can see that you recently lost a baby girl.” Being drunk and totally shocked, I couldn’t fight back the tears.

My ex-wife and I had lost a baby less than a month before. I’m normally opposed to any displays of emotion, as you can tell in Chapter 6. But this really fucked me up. All the sadness I had been hiding came rushing to the surface. I was fully crying, with a stranger on the beach holding my hand.

Bless her heart, she just comforted me until I could regain my composure. I still can’t thank her enough for that special moment. After the beach, we went home together. I never saw her again after that night.

I have a puzzle piece tattoo on my right arm. My ex has the other half. While we were in bed together that night, the palm reader mentioned the tattoo and expressed interest in doing one together. As I cuddled her, stroking her arm, I jokingly said, “That’s an entirely too intimate thing.”

I’m still looking for my next puzzle partner.

Before all my travels, when someone asked about my worst date, it took some brain power to think of one. I used to be very good at going out with women I had a connection with, so most of my bad dates were the typical stuff. There are two stories I used to tell my dates.

The first: we met on a dating app. Our first date was very normal. On the date, she told me her father was a big poker player, so much so that he’d get hotel rooms comped for free in Biloxi, Mississippi. Keep in mind we were in Atlanta, and Biloxi is a 5+ hour drive. After the date, we were planning our second.

We decided to drive her car to Biloxi and spend the weekend there. I know what you’re thinking: second date, and you’re going away for the weekend? Isn’t that a third-date kind of thing? Back then, no. Now, I think so. I’m very much in the moment. We’d had a nice time. Why not go to the beach and play poker?

I was also a huge poker player. My college friends and I would spend hours on it every week. In Georgia, gambling isn’t allowed. I believe that’s why I was so eager to go on a second date like this. Looking back, I should have just fired up PokerStars (an online poker website).

The 5-hour drive there was fine. I don’t remember anything off about it. We arrived at the hotel and checked in. After getting settled, she said she had a friend nearby she was going to see. I thought it was odd to go meet a friend right away, but I said it was fine. I’d hang around the hotel; just let me know when you’re done.

After a few hours of gambling, I texted her asking when she expected to be back. No reply. One hour went by, then another. I sent her another message: “If you’re not planning to come back soon, I’ll just do my own thing.” Not long after, she messaged me that she was still with her friend and asked if I minded if they came and hung out with me.

At this point I was already kinda annoyed. This is why you don’t go away with someone on a second date. I remember thinking, damn, I’m stuck here. If I had driven, I could just leave and drive back to Atlanta whenever I wanted. Also, the room was in her name, so I’d need to get another room. I decided to give it a little longer. I reluctantly agreed the friend could join us.

A few more hours went by. By now it was pretty late. Around 10 or 11, she and her friend finally got back to the hotel. I was very annoyed. I had spent my entire day gambling to kill time, waiting on her plan, and I hadn’t even had a proper dinner. She didn’t acknowledge that she had basically been MIA the entire day.

On top of that, she and her friend were wasted. I was completely sober and pissed. I thought to myself, the nerve of this woman. I attempted to make conversation with them, but it was pretty pointless. What eventually set me off: have you ever been a third wheel on a date? That was me at this point. She was having a full-ass conversation with her friend and not including me at all. I wasn’t interested in what they were talking about, but I found it extremely rude.

About 20 minutes into their conversation, I interrupted them. I said I was leaving and that they should both pack their shit. I ended up driving the friend home too, because I’m nice like that, and then I drove her the 5 hours back to Atlanta. She didn’t say a word to me the entire ride. I dropped her and her car off at her house, then drove myself home. We never spoke again. If I could do it again, I’d rent my own car, then either drive myself home or enjoy my time there.

The second bad date was a lot shorter, thankfully. I had gone out with a girl I was very interested in. I forget where we met. It’s not really important. I agreed to pick her up at her place and take her to dinner.

Once we arrived at the restaurant, she leaned in to give me a kiss. I was surprised but welcomed it. Kissing on the first date, before dinner, is extremely rare in the States. Years later, I’d learn that in Rio it’s the norm. I leaned in too, and our lips touched. She then put her hand behind my head and held me there. Our lips touching, nowhere to go. To make matters worse, her lips were pressed tight and not moving. I felt like I was being held hostage during our first kiss. I wasn’t able to enjoy the rest of the date, I was so traumatized by that kiss.

People always want to know the scariest thing that’s happened to me while traveling. Not all my wild stories involve dating or women. Plenty of mishaps happened on our guys trips abroad. Those hostage situations remind me of when my friend was almost taken hostage in Cancún, Mexico.

It started as a pretty normal trip. We spent most of our time enjoying the beach and sightseeing. One day we hired a driver to take us around. He was nice and offered to arrange a trip to see the pyramids at Chichén Itzá. We thought this was a better option than the big group tours, which left early in the morning.

The guy arrived at the agreed time with a very questionable van. I remember thinking, Hmmmm, not what I was expecting. My five friends and I looked at each other as if to say, I guess we’re doing this. We climbed in and started our two-hour journey. About an hour in, something unexpected happened: the van broke down. Can’t say it was a huge surprise. The fact that it made it an hour was a tiny miracle.

The driver told the one friend who speaks Spanish that something had overheated and we had to wait. We were all still pretty lighthearted, making jokes and laughing it off. After a short time, he gave the go-ahead and we continued. We did this stop-start dance a few more times before arriving, which turned a two-hour drive into closer to three. Our spirits were still high. We knew it wasn’t really under his control, and we eventually made it.

While we enjoyed the pyramids, he told us he’d asked someone to bring a different vehicle and promised it would arrive before we finished sightseeing. We enjoyed exploring, and when it was time, we headed back to the meeting spot. I looked over and thought, huh, this new van looks exactly like the other one. Twins? That wasn’t the case. It was the same van. At this point, we were starting to get a little concerned.

The group huddled up, staring at the questionable van. Should we go talk to the big tour groups? Maybe we could get on a bus and have them take us back. A breakdown on the way home would be sketchy since it was dusk and getting dark. We agreed to go with him, since none of us had the cash to pay him for the trip there.

Five minutes into the trip back, the van broke down again. It was almost comical how fast it happened. We all looked at each other like, Fuckkkk, this is bad. We continued this start-stop every ten minutes or so. By now it was night. Every abrupt stop escalated the tension inside the van. Six foreigners stuck on the side of the road in Cancún is a recipe for disaster. On our third or fourth takeoff, we got another fun surprise: a flat tire. I let out an uncomfortable laugh, like, sureeee, let’s add this to the list of things going wrong. You’d think he’d have a spare tire, but that would be too logical. He got on the phone and told us someone would come pick us up.

About an hour went by, and then a car appeared. Wait, it’s a car, and we’re six grown men plus the driver. How is this going to work? I still can’t understand what happened next. After the car arrived, the driver got out. Then another person, and another. The last was a woman with a young baby in her arms. Apparently he’d sent for his entire family to come. I found it hilarious that a man would bring his whole family to the middle of nowhere. I wasn’t worried about them. It was us or them.

Now that we had transportation, there was the problem of fitting all of us into a four-door car. We came up with a seating arrangement that Tetrised us inside. One friend and I had to sit back to back on another friend’s lap. I don’t even do tandem motos in Rio, so you can imagine my expression when this idea was pitched. We started the final leg home.

Once we arrived, I was exhausted. I asked the guys to take care of paying the driver and went to my room. The rest of the story is what I was told happened. On the way home, we’d agreed we weren’t going to pay full price. Why should we? If this had been in America, we might have been refunded. But this wasn’t the USA. The driver demanded the full amount, which none of us had in cash. Then a third car showed up after we were already home. It was basically the enforcer, there to make sure the money got collected. It took some of the guys to an ATM, and it was strongly implied that one of us, [S], would “stay” with the driver in the meantime.

We paid the full amount. A couple of the guys even got scammed at the ATM and were charged extra.

I actually regret missing this altercation. I’m told the third car had serious movie-gangster energy. What’s wild about that day is that, apparently, there had been a shooting. Someone on a jet ski had done a drive-by at the beach. We didn’t know it at the time, but maybe our driver was actually looking out for us.

People always ask what I do for fun. One of my favorite hobbies is watching sunrises. I love them because they’re peaceful, and the ones in Rio are exceptionally beautiful. Most people come to Rio and never manage to see one, which I find mind-blowing. It takes real commitment, because during the Rio summers I usually wake up at 4 a.m. to catch all the colors in the sky before the sun rises over the horizon. I’ve had two sunrises that always shock people when I tell the story.

The first was at Praia do Diabo in Arpoador, where I like to go in the summer months. It’s a very special place to watch the sunrise. There’s an outdoor gym, a tiny private beach, and a short hike to a view from the rocks.

One morning I noticed a group already in the water. It’s rare for anyone to beat me to the beach. Most people are still out drinking. Occasionally other enthusiasts join me, or drunk people who haven’t slept because they’ve been partying. After a longer look, I realized they were all naked.

It’s Rio. Nothing really surprises me anymore. I set up my canga (beach towel) and prepared to do yoga, intentionally facing away from the group. Naked people gallivanting in the water was sure to disturb my flow. A few minutes into my practice, I noticed a woman walking toward me. I figured she was just walking, but she was coming directly at me. Why is this naked woman coming to talk to me? By the time I was mid-mountain pose, she was standing right in front of me.

She began talking to me in Spanish. I was trying my best not to look at her breasts, but as a man, it was simply impossible. I understand some Spanish. She explained that she and her friends were enjoying skinny-dipping, as if that wasn’t obvious. I smiled and said, “No hablo espanhol.” She went on for another minute or two. I understood she was asking for my number, but I pretended not to. Not sure what it is about nudists, but they normally have bodies that should be hidden under clothes.

Eventually she went back to her friends, and I went back to my yoga.

The second time my sunrise was interrupted was in Morro de São Paulo. A friend and I had a long night and decided to catch the sunrise before going to bed. I went off alone to find a better viewpoint.

While taking in the view from the rocks, I noticed a man below me. I didn’t pay him any attention. From my peripheral vision, I could tell he was homeless, and it was obvious he wasn’t mentally stable. The sunrise was beautiful, with amazing purples and oranges streaked across the sky. There was also some nice cloud cover, which always makes for spectacular views. After a while, I started to hear a rhythmic skin slapping sound coming from his direction. I glanced over, and this man was full-on cranking it to the sunrise. I thought, wow, I love sunrises, but this is a bit much. I quickly went somewhere else and told my friends what had happened.

I’m still waiting to get an erection from a sunrise. Maybe a cloud shaped like a peach would do it.

A friend once asked me, “Wait, how many times have you been robbed?” I answered, “Too many to count.” It’s one of the sad realities of living in South America. Luckily, nothing has been at gunpoint so far, but I can’t rule it out. I’ve had my nice Levi e-bike stolen in the middle of the day because I locked it up by the basket, which they simply unscrewed before riding off into the Rio sunset. I’ve also had a very nice thousand-dollar gold chain pickpocketed, ironically on Thanksgiving Day, a year after I was drugged and robbed in Medellín. Apparently being robbed on Thanksgiving is an annual tradition for me. I’m starting to dread that holiday.

While expensive, these are an unfortunate part of everyday life here. You must always keep your head on a swivel. I’ve decided nice things aren’t worth having if they can easily be taken. I’d like to say I’m way more careful now, but I still live in the moment. I can’t walk around paranoid all the time that something will be taken, which is the exact opposite of me in a manic state.

I’d like to tell the story of my phone being stolen at Pedra do Sal, a famous samba party in Rio. Monday nights are especially busy because, traditionally, that’s when people had the day off. It was Christmas, and the gringo group of digital nomads had planned to have some drinks there that night. At the time, I had become friends with a very beautiful Russian woman with red hair. Let’s call her [Y].

A little about me: I’m very opposed to dating anyone in a friend group. The gringos in Rio have formed a large digital nomad community. It’s even been written about in the Rio news. While I was attracted to [Y], I knew it wasn’t a good idea to pursue anything. We had become good friends, and I didn’t want to ruin that. Plus, news of any relationship in the group spreads like wildfire. I wasn’t particularly popular, but I imagine this dynamic is common everywhere.

That night I spent most of the time chatting with [Y] about random stuff. I’d told the group I’d invited a date to join me. I could tell [Y] wasn’t thrilled about this, but we were friends, so I didn’t think much of it. My date arrived with another friend. She didn’t speak English, so I tried to talk with her through Google Translate. Pedra do Sal is extremely packed most Mondays, with everyone shoulder to shoulder, stacked on top of each other.

It’s not the best environment for long, deep chats on Google Translate, so I kept my messages brief. I wasn’t interested in her, though I’m sure she was a lovely person. As the night went on, I could tell [Y] was getting a little jealous. I found that surprising, because we’d never had anything romantic. I was getting ready to leave and saying my goodbyes. Not sure how it happened, but saying goodbye to [Y] turned into us kissing. It caught me totally off guard. I’m certain people saw us. My rule about not mixing business with pleasure had been broken. We talked for a second after the kiss. She confessed that she’d always liked me and that I was the only man in the group who respected her. I was flattered, but my inner dialogue was telling me to get out of there quickly so I could gather my thoughts.

I said goodbye and headed toward the Uber pickup spot, which meant walking 10 or 15 minutes shoulder to shoulder. If you didn’t know, Pedra do Sal is famous for pickpockets. I’m pretty sure one in three gringos who’ve gone has a phone-thief story. Normally I’m more careful with my phone, but that night I was a bit shaken from the kiss. I texted a friend who was coming to Rio and tried to explain what had happened with [Y].

Between texts, the person in front of me stopped walking and started moving backward. I quickly put my free hand on his back to keep him from coming into me. He kept walking backward. I stuffed my phone in my pocket and used both hands to stop him. This went on for several seconds. I was like, WTF, why is this guy walking backward like this?

Eventually we started walking again at a normal pace, still crammed shoulder to shoulder. A minute or two went by, and I went to grab my phone from my pocket. Surprise, surprise, it was gone. I briefly tried to look for someone who could have taken it, but it was pointless. At the time, I didn’t realize it had happened during the weird walking-backward situation. Looking back, it was a classic decoy.

One of the phrases I’ve been practicing in Portuguese is “Eu tô famoso,” which means “I’m famous.” Among all the digital nomads, I’ve become famous for being the guy who has things stolen. I’m just glad word hasn’t spread to the Cariocas (people from Rio) yet.

People on first dates love to ask whether you believe in second chances. I’ve never had a good answer. I might be about to find one.

Remember the girlfriend from Japan, the one who stepped out of my life after my episode? We ended up meeting again.

It was after my ex-wife and I separated, in the middle of the drinking phase of my grieving. I was out with my guy friends. I call them the Beach Bros. They’re friends, but we’re not very close. I wouldn’t expect a deep conversation about life from them, but they’re a great time if you want to drink or go out.

That night we were at Aldeia, a popular Sunday spot in Lagoa, or at least it was at the time. Every time I go out with the Beach Bros, I have a nice time, but I always catch myself judging them a little. The antics guys get up to when they try to meet women are entertaining, to say the least.

At one point I was wandering off to get another drink when I noticed a woman standing a little apart from my friends while her friend talked to them. She was secretly judging them, exactly like I was. After a longer look, I realized it was her. I laughed, because I always judge my friends when we’re out, and in that moment I thought we had that in common. Honestly, even if it hadn’t been her, I would have walked over and made a comment about it.

So I walked up, made a comment about what my friends were doing, and started talking. She didn’t realize it was me at first. It took her a second to figure out who was standing there. Then we said hello, talked about life and caught up, and exchanged numbers again. When we first dated, she was still learning English. By the time I ran into her at Aldeia, she had improved a lot. We never re-followed each other on Instagram, which is where she blocked me in the first place. It’s a small detail, but it’s one I noticed.

We went on another date a few months ago, and it was nice. We had a great time. We went out a few more times, and then I could tell things were getting serious faster than either of us could handle after reconnecting for such a short time. So I pulled the plug and stepped back. Maybe I was still hurt by how things ended during my episode. Maybe it was just too much, too quickly. I had just gotten out of a serious relationship, and I didn’t want to rush into another one, even though we’d known each other a long time and had a really good connection.

Fast forward to today. I’m going on a date with her again. This will be our third first date.

I reached out because I wanted to have a really good conversation with someone. Somewhere along the way I realized I’m kind of over the endless chasing-women thing, and I’d like something more serious. The guy who’s mostly harmless is ready to be a little more than that.

Before tonight, I sent her the Japan chapter. In it I wrote that I stayed silent to protect her, and that she heard silence and left. The last time I said nothing, I lost her. This time I decided to say everything, and I wasn’t going to sit across a table from her with that unsaid. She hasn’t responded yet, so I imagine it might come up over dinner.

I’m not sure what to expect, but I have hope. I won’t pretend there’s a cathartic scene coming where she explains everything and why. I don’t think that matters. What matters is that after all this time, and everything we’ve been through, we’re sitting across from each other again, and I think we’re going to have a nice time. I’m excited to see her, and to talk with her. I’m also curious how much she’s speaking now. I’m assuming she’s basically fluent at this point. I’m even a little excited to talk about the book, though I haven’t decided if I will.

I bought a new shirt, and I even ironed it, which says a lot, because I don’t like ironing. I managed to trim and shape my beard without incident, which is more than I can say for the last time I tried to groom for a woman. I accidentally trimmed off my eyebrows while trying to manscape, right before a trip abroad with a girl I was seeing. This time, I kept the clippers far away from my eyebrows. I’d like to say I got a haircut, too. I wanted to. I didn’t have time. So tonight, the shirt and the beard will have to do all the work.

We’re having dinner tonight. I’m going to finish this chapter so I can go meet her. Wish me luck.

If you’ve made it this far, I’m truly grateful you’re enjoying the read. I’m starting to realize that if this becomes a hit, any future dates will have an actual book on my dating history. I’ve had exes read my journal in the past. That was with my terrible handwriting. I joked to myself that if someone is willing to read that, they must really care about me.

This chapter is for my future wife. If I decide to get married. Or my next serious relationship. I’m hoping that sixteen chapters in, you’ve gotten a pretty holistic view of who I am/was at the time of writing this. One of my inspirations for this book is Modern Romance by Aziz Ansari. I’ve always enjoyed his comedy, so when a friend recommended I read his book, I jumped at the opportunity to hear him narrate it. Any excuse to be lazy and avoid actual reading.

What I enjoyed about his book is that it described how men in my generation feel when it comes to dating. I highly recommend getting a copy. It also made me sad, because most of the content made me feel sad about the current state of things. I’d love for phone calls to become a thing again, just to humanize the person you’re speaking with.

I’ve noticed a lot of the problems I’ve had growing a relationship slowly could have been solved with a phone call. It’s much easier to establish a pattern of only using written words to communicate. While I think this is great, it sets a bad pattern. The other person also has the same autonomy to be unreachable. But when you’re getting to know someone, it should be all-encompassing if possible: in person, FaceTime, phone calls, voice notes. The more data that isn’t written, the more useful. This is doubly true for me.

One of my best friends once quoted that the best relationships are when both people are interdependent. I hope I’m remembering that right. Each has their own life outside of the other, but there’s a healthy overlap of shared experiences.

What does the ideal partner look like for me? Very much a dating profile question. Let’s see if all my years of filling these out were helpful. It’s a seemingly difficult question, but for me I think it’s simple. I only need healthy communication and empathy for each other. I think everything else can be improved. Here’s what I refuse to treat as deal-breakers.

I strongly reject any of the superficial standards I’ve heard guys my age say. She must be young, fit, no kids, with a good-paying job. Sure, all that would be good. But time changes all. One day these things might not be true. Are you going to pull a Leonardo DiCaprio and drop them before they turn a certain age?

So, future wife, I actually don’t like calling you that. Let’s call you my muse. To my muse, this chapter is all about you. If you mention petty theft, or how your heart broke for me while you read certain parts, I already know you care more than most before even getting to truly know me. If you really want to steal my heart, you’ll ask me about my date where I took off my shirt to use it as an umbrella. I really want to become the man who puts jackets over puddles.