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

a. I think it means, when I was in the state of being into coffee after having gotten used to it, I went to Brazil

b. It describe the state not an action, so "When" is the same meaning as "During".

c. had gotten used is a past version of have gotten used(present perfect)

d. had gotten used is not working as past perfect. So, doesn't need an past event that corresponds with past perfect.

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

e. I think it means, The moment I got used to coffee, I went to Brazil.

f. got used to is an action verb, not a state verb, so "when" is the same meaning as "the moment"

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What's the difference between #1 and #2?

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You could say "had gotten used to" indicates you went to Brazil at some point after getting used to coffee, whereas "got used" indicates a more immediate departure to Brazil.

However, probably the more important distinction is in the difference in tone between the two sentences. First sentence is more likely to feel relaxed and like you were in no rush to get to Brazil. The second sentence doesn't necessarily indicate you were in a hurry, but it doesn't have the same laid back tone of the first sentence.

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