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Are the following two sentences interchangeable?

"Are you okay with that?"

"Is that okay with you?"

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    They are mostly interchangeable, however I'd recommend sticking with the 2nd option in most cases. The first question is asking if the person is okay; the second question is asking whether a proposal is acceptable. It's a subtle difference, but one to be aware of if you're dealing with a potentially emotionally-charged request/proposal. – Liesmith Aug 12 '14 at 20:47
  • They mean the same, and they're both pretty much the same in terms of "level of informality". But NGrams confirms my suspicion that the first version is even more recent and less common (it only really works if you understand okay as content, whereas historically it's more often been seen as equivalent to acceptable). – FumbleFingers Aug 12 '14 at 20:49
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Yes and No.

If you just want to be understood, then yes, go ahead and use them interchangeably.

If you want to show your English teacher that you understand the difference between subject and object, then unfortunately you'd fail at convincing her.

In this sentence,

"Are you okay with that?"

"You" is the subject and "that" is the object. Whereas, in this sentence,

"Is that okay with you?"

"That" is the subject (and therefore takes the singular verb "is" as opposed to those/these which would again take the plural verb "are") and "you" is the object.

I'm covering all of my bases with this answer, but sorry I can't give you a simply Yes or a simple No.

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