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Really Tricky Apostrophe Rules

January 9, 2020 by ProofreadingPal in Grammar

Last time, we dealt with the rules regarding apostrophes when dealing with singular and plural nouns. Some of these rules are so tricky, I caged them all together in this third (!) blog post on apostrophes.

So, we got through the “Possessives” section in The Chicago Manual of Style, 17th ed. to nouns plural in form, but singular in meaning (7.20). Up to that point, there was a sort of logic to the whole thing, but now we’re going to deal with the rules that are, for lack of a better word, downright wacky. If you’re going to be an expert, you’ll have to memorize these individually.

Sake (7.21)

If English usage weren’t wacky, then all “For so-and-so’s sake” expressions would follow the same rule. They don’t. Most of them, at least, use an apostrophe and an “s”:

For Pete’s sake
For appearance’s sake

But Chicago notes two exceptions:

For goodness’ sake
For righteousness’ sake

Joint vs. Separate Possession (7.23)

This one makes sense and is used often. When two or more people own the exact same thing, you only need an apostrophe and “s” on the last owner:

Gary, Devon, Misha, and Blanche’s book
ABC and NBC’s shared goals

When two or more people own the same type of thing but different actual things, all the owners get an apostrophe and “s”:

Gary’s, Devon’s, Misha’s, and Blanche’s various books
ABC’s and NBC’s different goals

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Compound Possessives (7.24)

Compound nouns like “baby buggies” and “know-it-all” get the apostrophe or apostrophe and “s” on the final word:

Baby buggies’ wheels
Know-it-all’s sneer

Double Possessive (7.26)

OK, this one’s tricky indeed. When you are saying that A owns many things, of which B is one, you use apostrophe and “s”:

A story of Shakespeare’s (meaning one of many)
A friend of Jenny’s

But when you don’t care how many others there are, you don’t use the possessive:

A follower of Freud
A codicil of the law

Possessive vs. Attributive (7.27)

This is one people get wrong all the time. The correct way to say it is ladies’ room and men’s room, but you’ll see the bathroom signs that read Ladies and Mens. If you go to Walmart, you’ll even see the chillingly awful clothing sections of Womens, Mens, and Childrens.

But to be correct, a group that owns something has an apostrophe or an apostrophe and “s.”


The confusion comes in when you’re talking not about a group that owns something but rather about a group that lends its name to something. This is now an attribute, like a ripe apple and a fashion plate. Thus:

Readers Digest
Knitters Club

Chicago gives great advice: “When in doubt, opt for the possessive.”

Possessive with the Gerund (7.28)

This is a doozy. In fact, I’m going to save this one for the next blog post. (Yes, that means a fourth blog post on apostrophes, but I’ve been meaning to do a post on the gerund for some time because, as I have said before, I am a huge nerd.)

Possessive with Italicized or Quoted Items (7.28)

Thank goodness, for italicized items this follows the general rule. Add an apostrophe for italicized items ending in “s,” and an apostrophe and an “s” for those that don’t.

Downton Abbey’s season four
The Avengers’ climactic battle

Best of all for quoted items, Chicago just suggests you avoid the whole apostrophe thing altogether.

Follower of “the golden rule”
Adherents of the “admire this blog post” rule

Julia H.

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