I may be very European, and grew up in a relatively chaotic city, but I find quite confusing when I’m on a grid city.

Yes, it’s sort of convenient at a rational level, but everything appears the same, and there’s no way to differentiate one cross from the next. Streets doesn’t have their own “personality” and you have to learn them by name. I don’t know half of the street names of the city I grew in, but I know where I am by the way they intersect and twist around in interesting shapes…

Or perhaps is just the way I’m used to

The approach is fundamentally different: in Europe it's organized by where you want to go (or do), in the US it's organized by cardinal directions.

In the US, if you're on 89th Street and 5th Avenue, and you want to visit your friend on 10th and 1st Avenue, you'll know exactly which direction to drive. Need to go to another city? Take the highway following the direction the other city is. Americans are typically good at knowing where the sun rises, or are always getting lost.

In Europe, you know your friend lives by the main hospital, so you follow the signs indicating the hospital, and then (if you're lucky) signs to your friend's neighborhood. From there you need to know how to get to the street they live on. Need to get to another city? Follow the highway signs indicating that city, if it's close by, otherwise you'll need to know what cities are on the way to it.

When we lived in the US, I could easily find any address in most cities. My wife was always getting lost, sometimes going to the complete other side of town.

We've been in Europe for over a decade now. She has no problems getting around to most places she needs to. I'm always getting lost going someplace new.

>Streets doesn’t have their own “personality” and you have to learn them by name.

I've lived in both types of cities, and actually even the most grid cities like Salt Lake City, have parts that are named as opposed to just numbered.

I prefer the numbered cities for finding way around.

Finally I don't think the everything appears the same is integral to it being a grid city, that is instead a side effect of American habits of rebuilding often so you end up with everything relatively new and in the same styles. That is to say the stylistic affect is orthogonal to the grid, although they are both found to coexist this is just a historical coincidence.

>I don’t know half of the street names of the city I grew in, but I know where I am by the way they intersect and twist around in interesting shapes…

I don't know where your city is, but I did notice many years before everyone had a phone I was in a class in Copenhagen and everyone in the class had lived in Copenhagen their whole life and then someone talked about an address and nobody knew where it was so someone had to go out to their car and get a book of maps.

Of course Copenhagen was also built to be potentially confusing to invaders, as I understand it, and I have often thought I was walking towards a particular destination to find I have either been walking away from it or perpendicular to it.

I also find that I prefer websites that are easy to navigate than ones that have character but are confusing. But I do prefer art that is apt to be confusing and intellectually stimulating to things that are simple and clear cut.

I think perhaps the problem is I just don't want going shopping in an unfamiliar part of town to feel like a surrealistic event.

I did agronomy work out in Kansas for a while, which is basically a big grid of very similar crop circles. Thinking on it, there were lots of places I passed by often on the roads, but would never remember, but wherever I stopped and entered a field on foot and discovered all the little differences in terrain that made each quarter unique, I was much more able to have a better mental map of where I was, even if I was only there a few times in a year.

Could it be that you learned the chaotic city better because you were more likely to go around on foot and experience little things, rather than just driving to a box store?