I remember when I stopped keeping track of my romantic partners.

I wasn’t so old - sixteen or seventeen, maybe. I hadn’t really had any sexual partners but, still, I kept this little notebook under my mattress - the yellow mini-legal kind, where you could rip a sheet clean off from the top. I always thought those were nifty. 

Anyway, I kept a list of the names of the girls I’d kissed. In hindsight, I’m not sure why I wrote them down - there weren’t enough people to require an organized system. No one ever forgets six names - especially those six names.

But, still, there it was. Six names and, next to each, a little asterisk for how far we’d gone. One star meant we’d kissed. Two for a feel up. Three for anything below the belt. I was a virgin - I had no system for actual, real, grownup sex.

Anyway, I came home from school one day and lifted my mattress to grab that old yellow mini-legal notebook and... it was gone.

My mother and I never spoke about it. She never brought it up. Still, I didn’t sleep for a week.

It took me a long time to figure out exactly why I kept that list. It was six people, after all. More specifically, it was six people who impacted my life in my formative years - there was no chance I’d forget them. Each one of them was a person with whom I’d formed a serious emotional bond. I was forming intimate relationships with people who mattered, and each person on that list would have been shocked to discover our relationship reduced to a name on a list.

I was bullied through most of my elementary and middle school years. I was ignored by girls and picked on by boys. The trend continued in my early high school years, but I was blessed to attend an all-boys private school. The bullying was contained. It was out of sight of the girls I met. And, simultaneously, I grew into a fairly handsome teenager. I was blessed with a charm with women I didn’t seem to have with men. Male friendships came hard but women came easy. It was a somewhat odd and complicated youth.

While I sat at the bottom of the pecking order in school, I suppose it felt good to exert a sense of power in some domain or another. And so I kept this list like Dexter kept his blood slides. They were these evil little token reminders of my conquests. Of my victories.

Anyway, that notebook became a late-night blushing memory by my twenties. By then, my personality had evened and I’d developed real and personal friendships of all varieties. A list of my conquests felt unnecessary and bizarre. A few times in my twenties, I was asked my “number.” Once or twice, it was by sexual partners but, usually, it was by competitive men who wanted to compare notes. I had to think about it each time. I had to decide whether I wanted to answer the question. And each time, they were confused by that.

“Oh, it’s so high a number that you can’t remember?” they’d say with an eye-roll.

Not really. It’s just that each time I had sex didn’t really feel like a victory. It didn’t feel like it was synonymous with the moment a person began mattering to me, or the moment they stopped mattering, or the moment I tricked them or beat them or won some invisible prize. It just felt like the logical evolution of where we were in our connection with each other. The sex was just a symbol of what we were up to - even if it was a temporary connection. Even if it was just for a night. Do I count the number of friends I have? Or the number of serious conversations I’ve had? Counting sexual partners seemed just as ridiculous.

I didn’t log it in a spreadsheet, real or imagined. Logging the number felt like conquering without recollection. It felt like ignoring the reality of the memory in favor of carving a notch in my belt.

Anyway, I inadvertently entered the realm of travel influencers not so long ago. I didn’t really mean to. I traveled abroad and it changed my life, so I started talking about it. I wrote a book about my journey and then I converted that book into a podcast, and then that podcast became my career.

During my trip abroad, I traveled through a whole bunch of countries, all of which profoundly impacted me in some way or another. I spent nearly three months in some places (Colombia). I spent two days in others (Panama). I have deeper emotional and spiritual bonds with certain regions and I have far inferior commitments to others.

I’m not quite sure how many countries I’ve stepped foot in. It’s not a high number. To level with you, I’ve counted it before but I keep forgetting because I just don’t care that much. And I don’t want to care that much. 

I road tripped the coast of Chile - from Arica to Santiago - over the course of six weeks. I still feel like I have unfinished business in northern Chile. I haven’t been south of Santiago, and I truly hope I dedicate a month or more of my life to exploring Patagonia at some point. But more than whether or not I do all that, I really hope I care more about the prospect of fully grasping a whole unified place than some future half-day layover at Heathrow in which I grab a drink at a pub and scribble England with a little asterisk in an old yellow mini-legal pad.

Anyway, I have plenty of “influencer” friends now. They all seem to have xx/197 in their bios on various social platforms. They wear that number like a badge of honor that indicates precisely how well-traveled and worldly they are. But I don’t think it communicates what they want it to communicate. It seems to paper over insecurity by asserting just how much of this world they’ve conquered. 

“I am a victor,” it shouts. “And these are my conquests.”

They don’t seem to give much thought to their relationship with each one of those numbers. They’re betraying that unspoken pact they’ve made with those places - those relationships they’ve formed or those relationships that haven’t fully formed. They’re marking notches in their belts before they’re fully grasping the depth of what those relationships - what those places and their impacts - have truly meant to them. 

I’m not quite sure what it is about the human experience that demands we keep track of our conquests. I’m not sure why we overcompensate for our shortcomings with spreadsheets and data that we think prove our strength but generally assert our insecurities. 

But we do. I do and you do, too.

I plan to travel to many more places. I have no idea how many places and I don’t know for how long. But I know I will fall in love with some. I know I will forget others. I know I will learn and grow and improve and keep becoming a better version of myself. And the bullying of my youth and the hardships of my adulthood will fall away naturally as I continue to hone my inner comfort in myself.

And, some day in the future, someone will ask me for my number. And I’ll say that I’m not so sure, but I’d love to tell you about the time I spent a month in Patagonia.


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Will Conway


Former political software guy. Now a traveler and adventurer, which isn't a job, and host of the @heybaggageclaim podcast, which really isn't either. Travel stories no one tells.