All too often, for example, I proofread letters from other people who in
their correspondence say that a meeting will take place in the future, say,
on Monday, March 21, 2006. Trouble is, March 20 is a Monday. The spellcheck
should check the day of the week versus the date and flag it with a red
squiggly underline as though it is a misspelled word to flag the error to the
document's author.

I'm surprised nobody has suggested this before, or have they?

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