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I just wrote a response on a meta Stack Exchange site to a question about tag usage and purpose. In that response, I found myself writing the following:

I hesitate to argue for the tag's (and the questions' that go with it) complete removal.

"Tag" is intentionally singular and "questions" is intentionally plural. Is that the correct way to use the apostrophe on "questions"?

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You simply should not have an apostrophe, at all, on "questions". – Joe Blow May 14 '11 at 12:34
@Joe Blow: If you drop that apostrophe there's no 'possessive' associated with questions, which makes the sentence semantically invalid, rather than just non-standard at the lexical level. – FumbleFingers May 14 '11 at 14:48
@Fumble -- not really. The sentence is a shambles - the grammar equivalent of those images you can look at two different ways. (Or perhaps, a Rorschach test!!) You're seeing it along the lines of "tag's removal" -and- "question's removal". Right? Rather it's a possessive that happens to be split up by a strange interjection: "argue for the tag's (by the way, those tags have abc and xyz and pqr, which would also be lost) removal". In the strange interjection there happens to be a plural, end of story. All the answers below, totally rewrite - the correct uber-approach! – Joe Blow May 14 '11 at 16:36
up vote 3 down vote accepted

This is a creative application of the apostrophe to avoid re-ordering:

I hesitate to argue for the complete removal of the tag (and of the questions that go with it).

It's not outright incorrect to apply the apostrophe in order to omit of, but it is highly unusual to qualify a possessive noun with a clause introduced by that, which, etc.; I think most would frown on it for possible ambiguity or lack of clarity in other situations. Still, I daresay I'm rather fond.

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Absolutely. OP's sentence may just about be grammatically valid by some reckoning, but it's so ugly I don't think any native speaker would use the form with so many 'ancillary' words. Simpler sentences, like I like Jim's and Bob's haircuts, just maybe. But not this one, please. – FumbleFingers May 14 '11 at 14:44
@Fumble Yeah, I'm not a native speaker. Totally agree that it should be re-worded, but I was curious nonetheless. – Adam Lear May 14 '11 at 15:24

No need at all for the apostrophe on your word questions

But why not

I hesitate to argue for the complete removal of the tag and associated questions


I hesitate to argue for the complete removal of the tag and its associated questions

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You're right the sentence really needs to be restructured, but per my comment against OP, it's incorrect to suggest you could just drop the second apostrophe and leave it at that. – FumbleFingers May 14 '11 at 14:50

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