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  1. I had gotten used to coffee, when I went on a trip to Brazil to try many different types of coffee.

I think this implies that I went to Brazil immediatly after I had gotten used to coffee. And When is the same as and it was that moment that~. When we mean this by when, we put comma. I feel like I can say when instead of before, when to emphasize the immediacy.

  1. I had gotten used to coffee, before I went on a trip to Brazil to try many different types of coffee

I think before is only talking about the time sequence without implying anything. Before means and it was after that moment that~. When we mean this we should put comma.

Do you guys think I tell the difference right?

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  • Would you please explain a bit more on context? The relationship/connection between two events, "get used to coffee" and "go on a trip"? Is the former considered as a condition/trigger/reason of the latter?
    – WXJ96163
    Mar 16 '20 at 3:23
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The way you have written these sentences is incorrect grammatically, but you are correct about the difference between them. You need to move when to the very beginning to make an introductory phrase:

  1. When I had gotten used to coffee, I went on a trip to Brazil to try many different types.

For the second sentence, remove the comma.

I had gotten used to coffee before I went on a trip to Brazil to try many different types.

We don't place a comma here because now "I had gotten used to coffee" is the main clause. You could also write,

Before I went on a trip to Brazil to try many different types, I had gotten used to coffee.

And now you see the comma again.

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The answer depends on the context.

context#1: fascinated

Assume you love coffee very much, the only reason you went to Brazil is coffee. You could say

When I had gotten used to coffee, I went on a trip to Brazil to try many different types.

To emphasize the fact that you're so fascinated with coffee that you were impatient to wait more, You could say

When I got used to coffee, I went on a trip to Brazil to try many different types.

context#2: prepared

Assume you're NOT that much fascinated with coffee, or the coffee is not the only reason to went to Brazil. Maybe you went to Brazil to visit friends or family. To emphasize the fact that you'd already gotten used to coffee, you were already prepared before that trip, you could say

Before I went on a trip to Brazil to try many different types, I had gotten used to coffee.

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