Anything strike you as weird about the following sentences?

“I shouldn’t like to punish anyone, even if they’d done me wrong.” That’s from George Eliot’s novel The Mill on the Floss.

Or, from another great English female author, Jane Austen, who in Mansfield Park has a character say, “I would have everybody marry if they can do it properly.”

Or how about a few lines of dialogue from classic plays:

“It’s enough to drive anyone out of their senses.” – Candida by George Bernard Shaw

“Experience is the name everyone gives to their mistakes.” – Lady Windemere’s Fan by Oscar Wilde

“God send every one their heart’s desire!” – Much Ado About Nothing by William Shakespeare

Each of these examples (and there are many more where they came from) violates a grammatical rule that is supposedly sacrosanct, which many of my editing colleagues still hold dear: that the pronoun “they” may never refer to a singular antecedent. In fact, not only is this not true of common conversational usage, but, as these examples show, it hasn’t been true for centuries in much written language, either, from the King James Bible to, well, all of Western literature.

It’s probably no coincidence that all of the examples above, including the quotes from novels, are in spoken dialogue, because English speakers have been using “they” as a handy alternative to “he or she” since Chaucer’s time, and any writer or dramatist who faithfully records how people actually speak is going to use it (even E.B. White, whose The Elements of Style famously forbids the usage, has a character in Charlotte’s Web say, “But somebody taught you, didn’t they?”). Most linguists trace the insistence on purportedly strict pronoun agreement, and hence the use of a generic “he” in indeterminate sentences like the ones above, to late 18th-century grammarians—a questionable attempt to purge supposed inconsistencies of usage, which, the same linguists love to point out, has never been applied to the evolving pronoun “you” (ever wonder why that singular pronoun always hooks up with plural verbs?). And it’s certainly true that in response to my examples above, you can find plenty of counter-examples in which “he” is used as the default pronoun for an indeterminate or unknown person, even prior to the 18th and 19th century. Increasingly, in our feminist era, you’ll see a lot of prose in which writers thoughtfully (but to my mind, somewhat arbitrarily) alternate that usage with “she.”

By now I’ve tipped my hand as to where I stand on this kind of common-sensical “they” usage: I’m all for it. If you want to read some long posts laying out the linguistic logic and history behind the position I’ve arrived at, knock yourself out; you can also find a very useful practical guide to dos and don’ts of the so-called “singular they” here. (I’m also persuaded, by the way, that implied or outright collectives, like theatre companies, rock bands, government bureaucracies, etc., should often or usually be referred as “they,” but that’s a slightly different can of worms.) Grammarians, you can address your complaints to rwkendt@tcg.org.

Before you do, you might want to hear about the next pivot in the story, and the real reason for this column: the possibility, which had honestly not occurred to me until it came up this past week, that the singular “they” might be used in another way that, like the examples above, seemingly challenges written syntax but which is probably worth our brains getting used to hearing and reading, as well. What about when we need a gender-neutral pronoun that’s not quite so neutral—that refers to transgender people who identify as neither female nor male? A pronoun that means, essentially, not an indeterminate “he or she” but a very definitive “neither he nor she”?

Alternatives have been proposed for this dilemma; the cabaret powerhouse Justin Vivian Bond, for one, has invented a new pronoun, V, and no less a publication than the New Yorker has obliged, but as that’s a personalized pronoun applicable only to Vself, it functions essentially as a proper name (in much the way progressive Christians like myself try to recognize the deity’s non-gender by saying, somewhat clunkily, “God loves God’s people”). In the hilarious and heartbreaking new play Hir, playwright/performer Taylor Mac—who identifies as genderqueer but accepts the pronoun “he”*—has a transgender character’s mother effuse, in the following exchange:

PAIGE: In these new genders, exists new pronouns. Max is no longer a she or a he. So you call Max, ze. You must use ze instead of the pronouns he or she and you must use the pronoun hir, H.I.R., in place of the pronouns her or him. Max gets very upset if you refer to hir as a she, he, her, or him. Ze wants you to refer to hir as a hir or ze. Ze also gets upset when you emphasize the ze as if commenting on the pronoun when speaking to hir. For example if you were to say, “What is ZE doing today?”, ze will not like that. Ze, understandably, is not to be treated as a side-show oddity. Ze wants you to say ze or hir as if this had been part of your regular speaking vocabulary your entire life. Any breach in decorum will cause hir to write in hir blog about how awful hir troglodyte fascist hetero-normative mother is. It’s fantastic.

ISAAC: I’m confused.

I was confused, too. What happened was this: A transgender performer about whom we’re writing in our October issue, in a piece in which gender is not a forefronted issue, requested that we use the pronoun “they” in reference to them—and as that last phrase shows, it is a much easier matter, grammatically speaking, to use “them” when the person remains a hypothetical subject, an unnamed “performer.” My brain can now easily digest a sentence, for instance, like, “A playwright writes about what they know.” It’s much harder, to my unschooled ear/eye, to accept that same construction once the subject has a name: “Jo writes about what they know.”

Honestly, that construction is bothering me less and less the more I read it and think about what it’s saying—and realize what a wider acceptance of such usage could mean to the entirely non-hypothetical subjects whose gender identity doesn’t conform to our grammar’s binaries (hardly a problem unique to English). I initially reacted negatively to that ostensibly “wrong” construction in a personal (but public) Facebook post, and received a rapid-response real-time education from friends and colleagues in not only how prevalent the use of “they” is for trans people in this context, but also in the stakes for those who claim it. As the brilliant music director Doug Peck put it, in response to my calling this new grammar challenge “a nightmare”:

I adore you, but that is the epitome of privilege! The *nightmare* is unsafely walking through the world in a culture whose language doesn’t acknowledge you. This conundrum you describe falls under inconvenience at best.

Point taken. But I also got this thoughtful response, from the great pop-culture journalist Mark Harris:

I won’t use “they” in writing—not the way you’re talking about. There are other ways to respect the identity of the person you’re writing about. As a journalist, I feel my first obligation is to clarity and accuracy—even before my obligation to the sensitivities and preferences of the subject…My feeling is that everybody has the right to be referred to without slurs or derogation, but that that’s not the same as the right to personally customized language.

I reached out to Polly Carl, editor at HowlRound, who is both transgender and an editor. And she—a pronoun she grudgingly accepts, she says, because she often finds “they” a confusing substitute in both writing and speech—wrote back to say that while it has never yet come up at Howlround,

I know if someone wanted to be referred to as they, we would do it, and identify it as their preferred pronoun, style guide be damned.

That’s where I’ve arrived at, essentially—including the crucial bit about explicitly noting that “they” is the subject’s preferred pronoun, either parenthetically or with an asterisk and footnote (I think this can and should be done without reference to the subject’s gender identity, so that that’s not forefronted if it’s not intended to be). You’ll have to wait to read our October issue and the story in question, but in practice it would be something like: “Jo writes about what they* know,” with a footnote reading, “*Jo’s preferred pronoun.” Without that small notation, at least for the time being, I fear that I and many of my readers will get lost in the grammatical weeds. Unlike Hir’s Max and Paige, we are not yet at the place where we can simply act “as if this had been part of your regular speaking vocabulary your entire life,” any more than we can simply drop ze or hir into a sentence. Sometimes leadership means recognizing where people are, all the better to bring them along to where we feel they ought to be.

As an editor, I live by rules, precedents, standards to guide my work so I can write, and help others write, with clarity and concision—Stoppard’s cricket bat speech comes to mind. I’d call myself a small-c conservative about these matters, in that I don’t believe that these rules should be idly or casually disregarded. But gender identity is neither an idle nor a casual matter, and language is deeply coded with gender (or is it vice versa?); new forms of gender identity and expression may accordingly demand new language, or at the very least adjustments to existing conventions. If I’ve been able to get used to a singular “they” in the contexts detailed above, what’s stopping me, apart from stubbornness (and yes, privilege) from following a similar learning curve in this new context? (It’s also quite true that the above arguments about the singular “they” seem trivial and academic compared to what’s at stake here.)

A colleague of mine thought we should simply have agreed to use the transgender subject’s preferred pronoun, “no questions asked.” But I’m glad I asked questions; I might otherwise have remained unpersuaded. If trans people of all gender expressions can teach us anything, it’s that what we need now are not new rules so much as a new flexibility.

*Mac has since made clear that the gender pronoun Mac uses is “judy.”