MediumThe City ChatGPT Promised Me. This was the place I had been waiting… | by Sophia M. Dai | Medium
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The City ChatGPT Promised Me

6 min readAug 27, 2026

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This was the place I had been waiting for — the city ChatGPT promised would fit me. I hadn’t heard much about it before and had pronounced its name incorrectly for months until an ex told me I was butchering it. I knew little about the country and only had distant memories of disliking their national team in the 2014 World Cup.

When I was thinking of leaving the United States for greener pastures, it was only one of two places recommended. Apparently, I was asking for a lot: safety, a stable and humane economy, progressive politics, no anti-foreigner or migrant movements, decent public transit, and livability. New Zealand lost on its higher cost of living and recent rightward shift. But what really stood out about Uruguay was how consistently the internet described its kind and humble people. After living in places where someone’s status and appearance often mattered more than the quality of their person, Montevideo seemed to offer something I hadn’t known to ask for.

I arrived in Montevideo off of a redeye from Bogotá to a slow, rainy Monday morning. It immediately struck me how quiet the city felt. I had most recently lived in Medellín where the aguacate man’s shouts were enough to get me up in the morning. I would later learn the influence here was more Spanish than Latin — asados started at 10 p.m. and nights ran into the next day. Though the calm at 7 a.m. was specific to the hour, tranquility was not an exception for the city with its peaceful, tree-lined streets decorated with elegant European architecture.

My art-deco Airbnb in Barrio Sur was merely three blocks from La Rambla, the city’s preeminent hub and walkway by the water. Slightly longer than a half-marathon — 13.7 miles — it spanned the length of the city. It was settling to see that view in the distance — knowing that the water was there, simply there, was enough to still the body. Looking at it, through tall residential buildings, it was often a murky brown. Hardly the glittering turquoise of the Bosphorus, the Río de la Plata was a sediment-full estuary and not the refreshing sea I had expected. I had sought beauty, but instead, found something that didn’t try to impress.

And this lack of performance, of vanity, was felt throughout the city. The streets were cracked, littered with stray dog poop and trash, and thick with smokers. The charm of the architecture was often tempered by crumbling walls and neglected facades. My Airbnb, though stylish, appeared to have been decorated in the ’80s and frozen in time. The linens were threadbare, the furniture old, and the air dusty. The people looked similarly understated. Most of the dress was casual, comfortable. Though not unkempt, it appeared that fashion and style were not the city’s first priorities.

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My first week in, I was already convinced Montevideo wasn’t the place for me and dismissed it for what I perceived as lack of effort. Patricio, a late-20s Uruguayan and my first local friend, agreed. Before I learned about his background or hobbies, he wanted to paint the picture of Montevideo that Western media hadn’t, describing the crime, increasingly high cost of living, and economic slump. He was preparing to emigrate because he wanted real career options and didn’t believe it was possible in his country, even with a college degree. “If you want to improve and make something of yourself, there are no opportunities. You can’t get very far.”

Patricio’s disillusionment with Uruguay perversely made me want to defend it. After all, hadn’t I come here for a reason?

“But you have safety nets built into the system. There’s universal healthcare. It has the lowest social income inequality in the region.” I rattled off facts I knew.

He laughed. “Haven’t you seen the homeless here?”

I had — and homelessness is a real issue in the city — but I had also seen my friends speak to the unhoused as equals, something I didn’t encounter back home. Walking through the Old City with a local, I met Víctor, an artist whose drug habit gets in the way of his art. He lives a transient life but he still finds a way to paint with community support. The quiet sincerity that moved through most of the people was visible — my neighbor who chatted with me in the elevator despite my hesitant Spanish, the young Uruguayan who insisted I check out the local Candombe drum circles in my neighborhood. I was laughingly taken aback when an old man at the market asked me to help him read the label on the carne packages. Did I already look like a local?

And a part of me wanted to adapt and settle into their gentle rhythm of life, the casual dress, the non-performative way of being. Even in gym culture, the focus was on the workout itself, rather than the posture. It was a relief after the intense fitness culture and beauty standards in Medellín and Istanbul. So for five days out of the week, I fit in. I dressed comfortably, I made myself unobtrusive.

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But by the sixth day, my outfits itched to impress. I wore white patent leather boots to my favorite wine bar’s anniversary party, bright coral wedges to a friend’s birthday party, and cream silk pants to lunch. Those were the times the stares came and asked, why are you trying? I found myself asking back, why don’t you try more?

To me, acceptance was a betrayal of agency. Agency was what allowed me to revamp my career and life multiple times over because I thought I could build something better. It was my greatest strength, but its cost was turbulence and constant disruption.

Now, I was in the eye of the disruption, recovering from a dream job gone wrong and grieving my resignation. I was rebuilding a life on my own terms, but the rebuild meant I was in the least successful period of my life. Less than two months into the sabbatical, I was already anxiously wondering when and how success would come. If it would come. I strove to find myself and simultaneously demanded validation of the me that was striving.

It wasn’t enough that I now knew I want to be a writer. I needed to become an acclaimed one. It wasn’t enough that I enjoyed much of Montevideo. I needed it to become the home that held everything. Instead of allowing myself to just write, I was already applying to MFA programs. I had hardly discovered my voice before I was pushing to have it “figured out.”

In my first week in the city, I met a man who would become my now-partner. At the time, we were both recovering from recent breakups and looking for a reprieve. Soon, we were spending full days and nights together, but every afternoon when I returned home, I felt a pang of guilt. Lying next to him, I chided myself. I was meant to be on my regimen — write, MFA apps, work out, cook and eat healthy, rinse and repeat. Time with Facundo felt like a safe cocoon after a hard year and bitter breakup. But I couldn’t enjoy its warmth and safety because I was too focused on what I wasn’t.

In the same way that I judged Montevideo, I judged myself. The lack of effort and ambition that I saw in the city was something I couldn’t tolerate in me.

This place asked if I could see it differently — that acceptance didn’t need to equal resignation. But sitting in stasis demanded a different form of agency, one that I hadn’t flexed before. This version didn’t force movement and simply stayed. Could I handle — could I accept — being unfinished? Unimpressive?

I was struggling with this feeling when my young friend, Juan, told me “Butterflies suck. They get all the glory but they’re just caterpillars with wings.”

His analogy confused me. Was I the caterpillar that was striving to be something else? I had always thought I was the butterfly.

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By the time I left the continent, Patricio would leave for Germany in pursuit of something he couldn’t locate at home. The “something” I believed he was looking for was a system that would allow him to improve his circumstances.

Like Patricio, I came to foreign lands looking for “something.”

But before I even understood what that “something” was — peace, acceptance, steadiness? — I wrote a list of demands. The criteria were important but they spoke to the extrinsic qualities we could see, the metrics that could be measured. What made Montevideo livable, what made it a place I could call home, was something that ChatGPT hadn’t promised.

It was the first place that allowed me to exist without wings.

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Sophia M. Dai
Sophia M. Dai

Written by Sophia M. Dai

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Writer, Former U.S. Diplomat, and Attorney trying to build a life worth settling into.