I’m Back With Medellin… But Will Things Go Deeper Between Us?
If you follow along in Twitter or Facebook, you probably know I returned to Colombia after my romp through Brazil.
I returned to that foxy lady, Medellin.
If you’re not up-to-date on my history with this lady, when we first met, things were amazing. I was absolutely taken with her and I subsequently packed up my bags and moved down to South America be with her for many months, including the first four months of this year.
She was impressive from the start and we made so many great memories together.

My girl is a piece of work.
But somewhere a few months ago, I decided we needed some time apart… some time to collect ourselves and think about what we want…
It wasn’t that I didn’t love her, I just needed some time. I think she did too.
So, I went gallivanting through southern Brazil, meeting a couple of new birds I found attractive, but none that really captured me as much as Medellin.
Towards the latter end of my stay in Brazil, I kept wondering to myself why I would choose to spend twice as much money to live in a place that didn’t jive with me as much as Medellin?
It would be insane.
So, I eagerly planned my return trip to Medellin a few months ago, and arrived, but this time with a certain questions on my mind…
- Could we really make this work, a gringo and a Latina?
- Could we really have a long-term relationship?
- Could this really be something significant?
Everyday I wake up in Medellin I feel happy. I feel happy just being in the city, breathing in the clean air, listening to the birds chip, and walking randomly through the city while seeing pretty girls come into view left and right.
And, in fact, the city itself (as well as Colombia in general) is beginning to prosper. Economic growth is happening year over year. Strategic trade agreements are being ratified. Many Colombians are moving into the middle class. And people around the world are starting to notice.
Medellin is gaining international recognition– for example, it’s in the running for the Wall Street Journal’s Most Innovative City in the World. So it is hardly a secret anymore. Dozens of US expats and internet entrepreneurs are showing up on a daily basis here, thanks at least in part to this blog (which I feel ambivalent about… more on that in a later post).
And of course, Colombia is just full crazy fun people. Kind, helpful, happy, entrepreneurial. Great to be around.
But some thoughts I have about my relationship with Medellin keep coming back…
- Part of me wishes this place were less well-known, with fewer backpackers and wanderers. I don’t like sharing her.
- Part of me wishes I had more money, so I could really skyrocket my lifestyle within the city.
- Part of me wishes my Spanish were at C2 proficiency (I’d estimate it’s at B2/C1 right now), so I could really get deeper into knowing this culture.
- Part of me still wants to explore (and live in) other parts of the world, including places very far from Medellin.
All of these considerations play a role in how deep I can go in this city. These all need to be dealt with, in one way or another. Otherwise my relationship with Medellin can only go so far.
For now, many practical realities remain ephemeral and uncertain if I continue with short-term stays in the city. For example, my awesome apartment won’t be available next time around, I’ll live in a different area of town, my friends will have different work / life setups and live in different places, and the hot girls (ahem, hypothetically speaking of course) who fall for me will keep asking me why I have to leave.
Initially, I was enthralled with just a surface-level knowledge of Medellin. The honeymoon phase was a blast, but the time has come for deeper considerations…
What is the life I’m creating, and is this city, this woman, going to be a part of it?


