Plurals

Q. I’m dealing with a quote within a quote. In fiction, a character in dialogue says something like, “You’re using a whole lot of ‘we’s’ here.” The “we” is supposed to be plural. How can this be punctuated properly? Or another case of the same situation, but in narrative text: A chorus of “got it”s, “yeah”s and way too enthusiastic “woo”s followed.

A. Often you can form the plural of a word used as a word simply by adding an s. That would work for your last set of examples:

A chorus of “got its,” “yeahs,” and way too enthusiastic “woos” followed.

But it works less well for “we” (mostly because “wes” looks too much like the name Wes). For that plural, either rephrase or use an apostrophe (as you’ve done in your question):

“You’re using ‘we’ a whole lot here.”

or

“You’re using a whole lot of ‘we’s’ here.”

Though apostrophes normally signal possession or contraction, they’re also good at clarifying the occasional plural that might otherwise be hard to read (as with letters: e.g., two w’s). Another option would be to use italics instead of quotation marks. But don’t put the s in italics (see CMOS 7.12)—and keep the apostrophe in we’s:

A chorus of got its, yeahs, and way too enthusiastic woos followed.

“You’re using a whole lot of we’s here.”

Switching to regular text for the s is analogous to putting the “s” after a closing quotation mark—as in “yeah”s. But “yeah”s is typographically awkward. Some styles allow it, so it’s a legitimate choice, but Chicago prefers the alternatives shown above (see also CMOS 7.13).

[This answer relies on the 17th edition of CMOS (2017) unless otherwise noted.]