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Is it correct to use are you sure and whether in the same question? For example, can you ask:

Are you sure whether you would like an apple or an orange?

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    The sentence is not exactly wrong and not exactly clear either. If I squint, I can imagine you want to know if your guest made the fruit decision. Then you want to know if the guest is quite set in that decision, meaning that there will be no changing minds on the fruit. Yes? – Yosef Baskin Jun 25 '17 at 20:12
  • "Are you sure whether you would prefer an apple than an orange?" Does make better sense, no ? – Baiwir Jun 25 '17 at 21:08
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    @Baiwir "Prefer... than...". Shudder. I am twelve and what is this. – RegDwigнt Jul 25 '18 at 9:05
  • As to the question proper, yes, you totally can use "are you sure" and "whether" in the same question. You just can't use them in the same question the way you did. You are trying to ask two things at once. That just doesn't work. Make up your mind which of the two things you're actually asking about, and then ask about that one thing. – RegDwigнt Jul 25 '18 at 9:08
  • @RegDwigнt at first i thought it was nonsensical, but after looking at a few google examples, it's clear that the question is equivalent to "have you made up your mind on what you want... do you want an apple or an orange?" I can see a waiter asking someone this question and someone responding without any confusion. – CoolHandLouis Mar 18 '19 at 5:27
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No, it is not correct. "Whether" is not used in this way. If you are trying to ask someone to decide between an apple and an orange, the correct way to do so is as follows:

Would you prefer an apple or an orange?

"Whether" is used when referring to a question indirectly. In informal speech, it can be often replaced with "if". The following are all correct ways to use the word "whether":

I asked him whether he wanted an apple.

I asked him if he wanted an apple.

I asked him whether he was sure he wanted an apple.

I asked him whether he preferred an apple or an orange.

Do you remember whether it rained last week?

Do you remember if it rained last week?

For more information on the use of "whether", see: https://dictionary.cambridge.org/us/grammar/british-grammar/if-or-whether

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That use is correct. Whether is used to introduce possibilities, but also to express doubts.

The sentence

Are you sure whether you would like X?

is properly formed. In your case X is the conjunction an apple or an orange.

See here the example

Are you sure whether a man has to reside in the district ten or twenty days?

used in the United States Congressional serial set, Volume 1269.

  • "Are you sure whether a man has to reside in the district ten or twenty days?" In this case, the question is asking the person if they know the answer and, if they do, to provide the answer. It's understandable, but it's a bit of an odd construction. – CoolHandLouis Mar 18 '19 at 5:42
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I think this is perhaps a non-standard colloquial form.

The question isn't just asking if they are sure. It's not a simple yes or no question. They are asking if they have made up their mind AND to tell them what their choice is.

Imagine a waiter asking this question to a customer. A typical answer would be one of: "yes I would like an apple", "yes I would like an orange", "no I need another minute", or "which fruit is in season?" Something like that.

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