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Given a sentence such as, "May 17-19 (is/are) available for our meeting," is it best to treat the "May 17-19" as a singular range or a plural number of dates?

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"May 17-19 are available for our meeting" should be right.

When you specify the dates in this fashion, it means you are referring to each day that falls in the range.

I wouldn't say that using "is" is always inappropriate, but that depends on the way you frame the complete sentence. In this particular example, I'd use "are". For ex: "any convenient day between May 17-19 is available for the/our meeting." Here I'm giving a range of available dates but I'm referring to only one day.

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Using the singular would imply that only one choice can be selected; here, the meeting will start on 17th May and continue till the 19th. Assuming you are not a disciple of the 'keep them at the table till they will agree to anything to get away' school of management, use are.

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+1: But note people do have multi-day meetings, especially if they have to travel a long way to meet each other. –  Peter Shor Apr 19 '13 at 0:28
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