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Person 1: "I don't understand what it is about."

Person 2 wants to know what 'it' refers to. She could say "You don't understand what what is about?" or else "What is it that you don't understand what it is about?"

The first is natural but feels colloquial and only really functions in a conversational context. The second is awkward and I'm not sure if it's even grammatical. Is there another way of constructing this question?

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    I'd say, 'What is the thing you don't understand?' – Alejandro Aug 19 '18 at 12:00
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Between the two sentences provided, the first seems fine and the second is ungrammatical.

There are many different ways to phrase the question in order to determine what it is.

I think the most natural question of all is to not refer to it in the first place, and just simply ask:

Person 2: "What do you mean?"

That will let Person 1 clarify.


But if I were to question it specifically, I would do it a bit differently:

Person 2: "What do you mean by . . . it?"

In live conversation, it would be emphasized with a pause and intonation. (My use of ellipses here is only meant exaggerate that.)

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