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I just encountered the following sentence which struck me as kind of strange:

you wouldn't know that to talk to him

I guess it means: "you wouldn't know that when you talk to him" or "if you talked to him" (but I am not sure).

My question
Is my interpretation correct? Which grammatical construct is that? Is it informal, non-standard or regional?

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    It's used. I'd say informal speech.
    – Lambie
    Commented Apr 20, 2016 at 16:32
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    It is a rather strange usage. I think (but don't know) that it's relatively informal, but I doubt it's "regional, dialectal" to any significant extent. My guess is it's a "shortening by deletion" from, say, You wouldn't know it if you were to look at him - but again, I don't know.
    – FumbleFingers
    Commented Apr 20, 2016 at 16:34
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    If the person about whom you are talking used to have a pronounced stutter but now does not have a stutter, you could say of him, "You wouldn't know that to talk to him." I agree with @Lambie that the wording is informal. However, if I were talking about that former stutterer, I'd say "You'd never know that by talking to him" (or "by hearing him talk"). To me, that sounds a bit more formal, not to mention correct. Don
    – rhetorician
    Commented Apr 20, 2016 at 16:46
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    Another variation: he's rich, but you wouldn't know it to look at him.
    – MetaEd
    Commented Apr 20, 2016 at 19:40

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Impossible to tell without a fuller context, but I take "that" to be a demonstrative pronoun, used to replace a thing that has been previously mentioned. So, for example:

A: His wife just died.

B: You wouldn't know that to talk to him [You wouldn't know his wife just died by engaging in conversation with him].

In other words, he doesn't mention that his wife died, and his demeanor does not indicate that anything like that has just happened. So, talking to him gives no indication of this situation.

If this is what you mean, there is nothing unusual about it. It is colloquial, but its meaning is clear.

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    It is particularly used for people with wealth who go to some length not to advertise the fact. They tell me he's worth tens of millions. But you'd never guess that to talk to him.
    – WS2
    Commented Apr 20, 2016 at 17:09

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