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I know the difference between used to and would. I've seen many examples of used to in questions, but I'm not sure if I've seen any for would. Are these questions correct to ask about someone's past habits, assuming the person who is being asked from is 60 years old.

Would you smoke when you were younger?

As a teenager, where would you hang out with your friends?

Is it possible to use would in this sense in questions?

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The problem with "would" is that it has lots of senses, such as forming conditional phrases or "future in the past". This makes your first example of a "garden path sentence". Your interpretation of "would" has to change:

Would you smoke... {I think this is a conditional, I'm expecting an "if" clause like "if it was healthy"}

Would you smoke when {hmm, the if clause is a when clause, perhaps "when no children are around"...}

Would you smoke when you were younger {what?? I'm lost. I was younger, so that would can't have been a conditional clause. I've been led "up the garden path" meaning I've been tricked I have to go back re-interpret "would" as meaning "habit". Now I can understand, but it is confusing.}

Garden path sentences are not good English.

The second sentence is not a garden path sentence. The initial "as a teenager" sets a past time context. So there is no way that the "would" could be conditional, and the interpretation is straightforward. So the second sentence is an example of good English.

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  • Brilliant! If I place the when-clause at the beginning then, the question will be no longer confusing and that'll be OK. Am I right?
    – Yuri
    May 9, 2019 at 20:35
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    You mean "When you were younger, would you smoke?" Yes that is less likely to confuse.
    – James K
    May 9, 2019 at 20:38

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