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Is the following correct?

Those with whom John speaks and who ask him about the new machine, are astounded.

Context: John speaks with random people, and they ask him about a new device.

I am aware of the who (subject, e.g. he/she/it) and whom (object, e.g. him, her, it) grammar rules. I believe that the sentence is correct but still, it looks strange to me.

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To answer your actual question: Yes, that sentence is correct.

It does sound a bit odd to use both "who" and "whom" to refer to the same thing in the same sentence (and many native speakers I think would also think it "looks strange"), but even so, this is in fact the correct way to say that.

I think because it is unusual enough that it seems a bit strange, many people would probably choose to break up or rearrange the sentence somehow to avoid it, but it's actually perfectly fine to use it this way too (and does show off that you know your "who"/"whom" rules, probably better than most native speakers do, actually).

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Modified from Grammarly: "Who" refers to the subject of a sentence. "Whom" refers to an object of a sentence or of a preposition phrase. An example using both forms:

Who is on first, and to whom should I give his paycheck?

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