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Learning a new language: "Why are there two words that both seem to mean 'very' in this language? How am I supposed to know which one to use?"
Speaking English: "There really should be a word between 'amble' and 'stroll', 'meander' isn't quite right."
@pganssle One of the teachers of my Japanese classes in grad school said that this sort of thing was one of her favorite parts about teaching the language: All of the questions that come up about subtle differences between this or that word or phrasing, that as a native speaker she never would have otherwise thought carefully about and tried to explain.