Mostly Harmless

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.