AI AND ROME! WHEN ARTIFICIAL INTELLIGENCE TRIES TO UNDERSTAND A CITY THAT REFUSES EXPLANATION
THEY SAY ROME DOESN’T NEED EXPLAINING. IT NEEDS TO BE LIVED. BUT WHAT IF ROME LIVES YOU FIRST? THIS TIME, MY TRAVEL COMPANION WAS CHATGPT. THAT’S WHEN I REALIZED WHAT IT LOOKS LIKE WHEN NIGHT LASTS FOR DAYS – AND KEEPS GOING.
Word:
Danilo Mašković
Photography:
Stefan Miloš
Date:
19.1.2026.
I think there’s no harder question than the one people keep asking me: “What’s your favorite place?” I’ve never had an answer. As a master of deflecting conversations, I usually recall some travel anecdote and build a story where none was asked for. Sometimes I even ask myself: what place is it, really? And in which year did it even happen.
I mostly remember things like an elephant. (If I didn’t like elephants, I’d probably dispute that claim too.) And sometimes it feels like I haven’t even lived my own life. That depends on the mood. People who know me are familiar with that trait. But a place? A place was always someone – a friend, a brother, a sister, a passerby, accidental or intentional. They made the journeys. They were the favorite cities. The favorite theaters. The favorite restaurants. That’s exactly why Paris on a Wednesday can feel mediocre, while Zagreb on a Tuesday can be an excellent night out. (Any resemblance to real events is entirely intentional.
Over time, I learned that I always remember the companion first — and only then all those “Colosseums.” It took me a while to become aware of that. Maybe Rome itself would have been different without all those people. Or maybe I would have been different without Rome. Both are true. And neither exists without the other.
This is also the legend of Madame LaLuce. She knows she is Rome. And that’s simply how it is. Every espresso, every breath, every paving stone, every sleepless night — she’s in all of it. Rome is her. And I am always a little more myself when I’m with her in that city.
It’s quite late, and I like to linger at night. The city glows in the distance. I reassure myself there are still others awake. And there were…
COME POSSO AIUTARTI?
Me: Can you explain Rome to me?
ChatGPT: Rome is the capital of Italy, known for its rich history, architecture, art, and cuisine. Symbols of the city include the Colosseum, the Roman Forum, the Vatican, the Trevi Fountain…
Me: No. Don’t lead me into a brochure. Try explaining that feeling when you sit on the edge of a fountain and the water murmurs like a sentence someone never let you finish.
ChatGPT: Based on available sources, the feeling you’re describing can be associated with nostalgia, longing, melancholy…
Me: That’s not an emotion. That’s Rome.
That’s the moment when you’re sitting on the Spanish Steps (back when it was still legal), and someone is silent at you with their eyes and you know that silence carries more meaning than any loud “Ciao bello!”
ChatGPT: Would you like me to create a personalized walking route in Rome based on your interests?
Me: I’m interested in a route to a place that no longer exists. To the bar we called Pace – now living only in the air. I’ve heard it reopened its strangely closed doors. I need to check that myself. What I really want to know is how to write down that moment when you can’t tell whether the smell of rain is coming from nearby pine trees pini di Roma or from fresh paint in an apartment where someone is restoring a vintage furniture collection.
ChatGPT: I’m sorry, I can’t locate all of those places. Would you like me to search for alternatives nearby?
Me: You don’t need to search for anything. Just stay here. And listen.
CHIEDI QUALSIASI COSA
ChatGPT: Alright. Take me through your Rome.
Me: First rule: forget plans. Rome laughs at them.
For example, I wanted to visit the Baths of Caracalla, a place not everyone puts on their list. There must be a reason for that. But instead, I ended up at Jane’s studio – JaneDoes. Wine was poured into mismatched glasses, music from someone’s childhood played in the background, we looked through projects and vintage décor collections, and talked about the City. Some things you can even take home in your carry-on luggage. (Did I bring something back? I did.)
ChatGPT: So, nothing classic then?
Me: Only if it’s on my terms.
I went to the keyhole on the Aventine Hill. I waited my turn, it was around 28 degrees, a few people ahead of us. And then – that scenographic perfection: St. Peter’s Basilica, framed perfectly. Silence. That was the only “selfie” I took that day – for myself, not of myself. I don’t write guides. I write situations.
ChatGPT: Situations? Like… a mild fistfight on Piazza Navona?
Me: How do you know about that?! Piazza Navona used to be our film set – once even a ring. There was a night club in a narrow street behind it. A favorite at the time. I’m convinced all that charged energy has something to do with those two quarreling artists and their works – fountains clashing with the Church itself. In my life, art always imitates life.
And you know what? If Emily in Rome had existed, I would’ve written the script for them. A missed opportunity for me, and especially for them. That’s my short and sufficient review of that TV (non-)achievement.
ChatGPT: And where would you stay?
Me: If I weren’t staying with friends, I’d choose The Monastero Collection Roma, near Circus Maximus. Once a monastery, overlooking the Palatine Hill, after which palaces are named, just so you know where you are. Here, your heart beats slower — but stronger. A courtyard where you can hear your thoughts moving. Walls that could literally speak, but never feel frightening. My favorite hotel moment? I make a Nespresso, sit by the window, and look at the palace. That’s how the nuns once did it when this place served them.
Next door, there’s a museum dedicated to culinary history, an essential layer of this city.
In Garum, I found a dinner recipe from 1732. I can’t wait to give it to Manda, so we can finally eat like Roman emperors. They also host a vintage festival here, vintage culture is incredibly strong in Rome, so good shopping is guaranteed.
(Chat pause)
I recall stepping outside the hotel gate with a glass of prosecco, pausing meaningfully, crossing Via dei Cerchi, and finally toasting the Great Circus.
What a feeling.
ChatGPT: After all that, you must get hungry. Where do you eat?
Me: Depends on the time of day. In the morning, I’d send you to Bar Farnese, to an old gentleman in his 80s who’s worked there since he was 18. I’m sure he’ll make you a perfect cappuccino, and a sweet Roman breakfast that fuels you until early lunch. Then you always – always – get lost in Trastevere and find a place without a tourist menu. They exist. Trust me. Just rub your eyes and your stomach, a little. Conceptually, you might start at Da Enzo al 29, end up with a Negroni at Freni e Frizioni, and finish with an (alcoholic) dessert at Teatro e Cioccolata. That loop, that’s where everything aligns for me.
ChatGPT: The most beautiful view of Rome?
Me: La Grande Bellezza. Opening scene. The Gianicolo viewpoint. You look at Rome the way you look at your past lives. I have nothing to add. After that, you toast the moment at Bar San Calisto. Continue the experience. I used to drink half-liter Peronis there. Still do. Only now the bar owners probably live a bit better – and that’s fine.
ChatGPT: So, is Rome your favorite place?
Me: Yes. But not because of the Colosseum. Nor because of tiramisu.
Because of LaLuce.
Because of white smoke.
Because of those days when you’re searching for nothing and find everything.
Because Rome is like an old friend who always tells you the truth, without judgment.
Because it’s the only city where I know how to be silent without feeling alone.
ChatGPT: And when you think you’ve fully understood it?
Me: It changes language.
Or rhythm.
Or the corner you thought you’d already been to.
And then – you stop asking.
And let it speak forever.
(Chat pause)
I thought of the Pope. That departure…
I can’t explain it, but everything that truly brings me joy in life contains that moment of eternity (and yes, this realization cost me many therapy sessions).
We’re waiting for the white smoke.
A theatrical confirmation that the world is, after all, still turning.
My current white smoke is www.stefanmilos.com.
May the Holy Spirit of design descend upon everyone who clicks.
Amen.
