Going to the city

As you know, I used to live in a place we called Clove Island, and now I live on Volcano island. The languages aren't the same, but they're very similar. I could go on for quite a bit about the specifics of the differences, in accent, vocabulary, verb conjugations, etc, but chances are I'd bore you, so we'll skip over that. In summary for the paragraph I started to write and deleted multiple times: islanders can often understand each other, but it's not always easy.

But the funny thing about understanding another person is that we sometimes think we understood when we really didn't. In English, we assume certain understandings based on what we know of someone's context. Take the following sentence, for example:

"I went to buy tomatoes, but my buggy broke and I spent a long time fixing it."  

 If the person is Amish, we understand that they were driving their horse and buggy somewhere to buy tomatoes, the buggy broke, and in order to complete their trip they were obliged to spend time fixing it. We might wonder why they would buy tomatoes instead of growing them, but fixing the buggy makes sense.

If, on the other hand, the person is from Louisiana, we understand that they went to the grocery store, were stuck with an unfortunate shopping cart (buggy), and decided to spend a long time fixing it before buying their tomatoes and going home. The question we ask ourselves, or them, is instead: why did you bother fixing the buggy instead of just grabbing a different one? 

So, did you understand the speaker's intention? It depends entirely on how familiar you are with their context. 

Here in the islands, there's a phrase you hear fairly often, but depending on where the person is from, the meaning could be the opposite of what you think. "I'm going to the city." 

Which city is that? It depends on who's talking. If they're from Clove Island, it means they're leaving home to go into the capital city, or leaving the homestead to go into town. BUT if they're from Volcano Island, they mean that they're LEAVING the capital city and going to their hometown. In fact, it's the exact opposite meaning depending on which island you're from/which language you're speaking. 

Wait, what? 

So, when people ask me how well I understand the language on Volcano Island, I have to include situations like this - have I figured out the places where I think I understand but actually don't?