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I bumped into him on my way back home. He wanted me to ask you how you were doing.

I bumped into him on my way back home. He wanted me to ask you how you are doing.

Are both the above sentences grammatically correct?
What's the difference in their meaning?

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Both sentences are correct and mean the same thing in all contexts as far as I can see.

He wanted to know how you were doing. The normal rules of reported speech are used here - wanted and were doing both occur at the same time. Compare:

He wanted to know if I was British. There is no suggestion that I am not British (and British nationality cannot be revoked, or lost). The speaker and listener both know the rules of reported speech so there is no misunderstanding.

However, at times confusion can arise if the tenses are always moved back:

The radio operator said your husband is alive is a better way of reporting matters than The radio operator said your husband was alive.

Arguably, saying He wanted to know how you are is more effective than the alternative as it is very clear.

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Both sentences are correct and understandable.
To my AmE ear, I would say that

He wanted to know how you are doing

is a question about how you are and if you are ill or have any problems

He wanted to know how you are

whereas

He wanted to know how you were doing

is a question about progress you may have made in a task

He wanted to know how you were coming along with writing your paper

But that may be stylistic, usually both will mean the same, that is how you are getting on, any ambiguity is usually resolved in any followup context.

  • Oddly enough, this appears to be explicit. Except, of course, the idea of your saying something to your AmE sounds a bit comical. – Ricky Dec 28 '15 at 19:51

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