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Which Sunday do you prefer, if Sunday is OK with you?

Is the above sentence grammatically correct and natural? I'd like answers both from BrE and AmE speakers.

Sorry for my short, abrupt question. I do have my own opinion about this issue, but I'm remaining silent on purpose in order not to mislead you into saying things in favor of my potentially preconceived ideas.

By the way, I've asked the same question elsewhere as well. It's not that I don't trust the answerers there. It's just that the English learners around me may not trust me as a reliable source of information about the English language. I've been giving them my answer but they probably need confirmation from multiple sources.

Please note I'm not asking you to proofread the text. I wanted to ask you if the usage of the second "Sunday" is grammatically correct, idiomatic and natural. I was thinking that the usage of the second "Sunday" was wrong. It sounds unnatural. It is because, to me, it seems that if the speaker wants to ask whether there is any Sunday the other person is available, then (if he has to use this structure at all) he has to say "if a Sunday is OK with you" (with an indefinite article in it).

Thank you very much for your time.

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    Please specify what concern you have with the sentence: as in, which part do you think someone might find ungrammatical and why? This is necessary to prevent this question being closed as "proofreading request" which is off-topic for this website. – English Student Feb 17 '18 at 10:10
  • Oh, sorry. I'm not asking you to proofread the text. I wanted to ask you if the usage of the second "Sunday" is grammatically correct, idiomatc and natural. I was thinking that the usage of the second "Sunday" was wrong. It sounds unnatural. It is because, to me, it seems that if the speaker wants to ask whether there is any Sunday the other person is available, then (if he has to use this structure at all) he has to say "if a Sunday is OK with you" (with an indefinite article in it). – OED Loves Me Not Feb 17 '18 at 10:14
  • Thanks for clarifying. I am not sure which is the correct form of the sentence but somebody will certainly help you. Please edit that explanation into your question before somebody closes it for proofreading! Edit: I did it for you myself. – English Student Feb 17 '18 at 10:32
  • You are most welcome @OED Loves Me Not and we members are always happy to help you here on English.StackExchange.com! – English Student Feb 17 '18 at 10:56
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    Note that 'Is Sunday OK with you?' is ambiguous and needs context to disambiguate the meanings 'Is this Sunday OK with you?' and 'Are Sundays OK with you?' Your sentence disambiguates by forcing the non-specific sense of 'Sunday'. It remains problematic without other previous context: what is being planned, and why are Sundays being singled out. – Edwin Ashworth Feb 17 '18 at 11:42
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You are right to suppose that "a Sunday" is the most proper construction here. However, the most formal version of the sentence would then be

which Sunday would you prefer, if a Sunday is all right with you?

The use of "OK with you" already makes the sentence somewhat informal, so the lack of 'a' before Sunday is permissible and does not at all change the meaning:

Which Sunday do you prefer, if Sunday is OK with you?

Also, Sunday is rather being used as a generic name for a certain type of week day here (there are 7 'types' of which one is Sunday) as in

Which pizza do you prefer, if pizza is OK with you?

You don't need to say 'a pizza' here or 'a Sunday' because the 'a' is implied in the sentence. Some people would say "if Sundays are OK with you."

Regarding your concern about the meaning of the sentence "Which Sunday do you prefer, if Sunday is OK with you?", it would be typically interpreted as your asking someone whether Sunday is OK with them and if so, which Sunday would they prefer? If that is the meaning you intended then the sentence is very clear. If Sunday is not OK with the other person, they will let you know.

  • Thank you very much, English Student, for your detailed explanation. You've enlightened me a lot. – OED Loves Me Not Feb 17 '18 at 11:13
  • You are most welcome @OED Loves Me Not and you can read many more useful questions and answers about English collected over 7 years on this website. – English Student Feb 17 '18 at 11:15
  • And the second 'Sunday' is necessary if you're clarifying which day. 'Which Sunday, if it's okay with you?' Can also be understood to be questioning the event itself, not the time. – marcellothearcane Feb 17 '18 at 12:40
  • Thank you, marcellothearcane. Am I then to understand that the second "Sunday" in the captioned sentence (Which Sunday do you prefer, if Sunday is OK with you?) should mean "next (this) Sunday"? In other words, could you please tell me what exactly the captioned sentence should mean? – OED Loves Me Not Feb 17 '18 at 21:34
  • Now added into my answer, based on your latest comment, please see @OED Loves Me Not: "Regarding your concern about the meaning of the sentence "Which Sunday do you prefer, if Sunday is OK with you?", it would be typically interpreted as your asking someone whether Sunday is OK with them and if so, which Sunday would they prefer? If that is the meaning you intended then the sentence is very clear. If Sunday is not OK with the other person, they will let you know." – English Student Feb 17 '18 at 22:53
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Your sentence is grammatically correct but awkward, due to its phrasing and repetition of the word, Sunday. While purely a stylistic preference, this sounds more articulate to me:

If Sunday is OK with you, which one would you prefer?

It flows concisely, so it is reasonable to expect it would be easier to understand. I'm sure there are other, equally correct ways to say or write the same thing; however, eloquent language involves sound logic and rhetorical technique as much as grammar.

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It's correct.

More natural/idiomatic:

Are Sundays good for you? If so, which Sunday do you prefer?

That's one formulation among many.

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