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Is it possible to ask about the part after "that" ?

What are you sorry that you couldn't do?

Where are you happy that you will go?

What friend of yours are you happy will come to visit you?

  • Your third example is missing "that" – Peter Jun 28 '18 at 13:10
  • They're all "syntactically valid", but even the first example is a bit "convoluted" for normal conversational contexts, and the others are progressively even more so. In practice people would usually simplify the syntax to You're sorry you couldn't do what?, You're happy that you'll go where?, You're happy that who will come to visit you? (with heavy stress on the highlighted wh- words). It's just too much trouble to try and include which of your friends in the last example - and it probably doesn't represent necessary information anyway, so I'd just discard it. – FumbleFingers Jun 28 '18 at 13:12
  • @Peter: The third example is very clumsy, but there's no simple way of rephrasing it to validly include the relativizer that. – FumbleFingers Jun 28 '18 at 13:15
  • @Peter I didn't forget it, because, it should be like that. – Jawel Jun 28 '18 at 13:19
  • What is the reason that you ask questions like this? (It seems like you're trying to better understand a concept you are learning from a book, but you don't provide any background information, so it's hard to tell. More information would probably be helpful for everyone.) – J.R. Jun 28 '18 at 14:00
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They are all grammatical and idiomatic. This can be an emphatic form of the question, letting the listener know either that you caught most of the sentence but not the key phrase, or that you found what you just heard to be incredible or at least surprising.

What are you sorry you couldn't do?

You are sorry you couldn't do what? Did you say "taste BBQ'd tyrannosaur brisket"?

Where are you happy you will go?

You are happy you will go where? Did you say "a furry convention"?

What friend of yours are you happy will come to visit you?

You are happy what friend of yours will come to visit? Did you say your college roommate?

This construction could also be a form of "standard question".

To join this club, you will have to answer several questions that are always asked of people who wish to join:

What are you sorry you couldn't do?

Where are you happy you have gone?

What friend is it of yours you are sometimes unhappy to see?

P.S. You could introduce these clauses with that (that you couldn't do, that you have gone, that you are sometimes unhappy to see).

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