I get a weekly update from a certain biz/marketing guru who shall remain nameless. I like her work, generally, so I don't want to seem ungrateful for the gems she shares with us.

And I will, if I name her, because I'm gonna read (but not drag) one of her latest posts about how to improve your website copy.

In the advice she gives in that post, she's missing a big secret, and it's something that I used to teach even my introductory-level English students. So regardless of whether you're an entrepreneur trying to get more hits or a freshman in college trying to understand why this writing class that you're forced to take even exists, this post in the Oratoria is for you.

It's the Rhetoric, Folks

Take a look at my second sentence in this post:

I like her work, generally, so I don't want to seem ungrateful for the gems she shares with us.

This sentence is rhetorically off the mark. How so, you ask? My English 101 students could have told you.

On day two (or so) of English 101, I told (NB: I don't teach anymore) students about rhetoric. Aristotle defined it as the art of knowing the available means of persuasion in any given situation. Today's rhetorical studies is less concerned with persuasion than with "communication of meaning," which encompasses persuasion. But the rest of the basic elements are still important. Based on that definition, what can we see that Aristotle emphasizes?

Audience: In order to persuade someone, I have to know what they believe, think, like, are moved by, etc. In order to communicate with them successfully, I have to know what language they speak (even better: what dialect of that language), what their mood is, what they care to hear about at any given moment, etc. I have to know their motivations for listening.
Topic: What am I trying to persuade them of or communicate to them? What are the details of that topic that they'd be interested in? Uninterested in? Repelled by? Curious about? Aristotle spent hours and hours lecturing about how to appeal to very specific demographics of the typical audiences that his students might encounter, as proven by the hundreds of pages of class notes from his lectures that now comprise his Rhetoric.
Purpose: Why do you want to communicate? Why is the other party listening and, perhaps, responding in a specific way? What are you trying to achieve?

Those are the basics. For any given item of writing--from a grocery list to War and Peace--my English 101 students knew how to break down any communication and understand it rhetorically.

In my sample sentence, there are a few problems, mostly to do with audience. First, I don't identify who "us" is. Secondly, I seem to assume that my audience will be persuaded by my discussing what I like, which is the topic of that particular sentence. Speaking of topics, that sentence is shaky, because its topic seems to be what I like, while the rest of the introduction of this post is headed in a very different direction. That set-em-up/switch-em-up approach isn't always problematic, but it's certainly risky, especially vis-a-vis purpose. Why did I need to do that re-direct? Why did I need to explain what I like and don't like? Why did I need to shift gears suddenly thereafter?

This is, admittedly, a very, very close reading of just one little sentence, but my point is that my English 101 students were equipped to do that.

Oh, the Errors You'll Catch

So I'm watching this video post by this guru, and she's giving out very helpful advice: people should write their businesses' websites with the customer in mind, not themselves. What does that mean? Well, for example, my "About" section on this site is tucked away behind two pages; it's past the page about my company, Laughing Saint Editorial LLC, on a sub-page of that sub-page. Why? Because what I do for a living is about providing a service, not about providing a spotlight for myself. It's you, the customers and readers, who come here looking for (here comes purpose) information about my services and about how to survive in the usage jungle. (NB: Someday, I'm going to write a book titled Oh, the Errors You'll Catch: How to Survive in the Usage Jungle.) So instead of writing about how I like copyediting, I write about what my services are and what they provide to you when I'm writing the main pages. I do the same thing for my clients: your website (rather than your LinkedIn profile) is about your customers, so I'm going to write your website copy with a lot of "you" and "your," a bit of "our" and "we," and almost no "I" or "my."

The guru, in explaining that, was 100% right.

But, right at the very end of the post, she mentioned that being "cute" and funny on your website is pretty much required for catching customers today.

Woah, there. Not so fast.

Clearly, she knows her own audience: they like her quirky style, and her brand is all about being personable. Her audience expects this, but not all audiences are her audience. Not all industries are her industry.

If I'm writing a website for someone in an insurance firm, I will not be using cute, funny copy on the website. If I'm writing a website for a financial-services firm, I will not be using cute, funny copy. If I'm writing a website for a community organization dealing with emergency services, I'm not going to use cute, funny copy.

Why not? Because it wouldn't serve my purpose. It might confuse readers, because rhetoric also includes issues of tone, genre, and timing. If you're looking for a bankruptcy attorney, do you want that person to be cute and funny when they're trying to solicit business? Apparently, this guru thinks you do. My experience says differently.

Research and Field Testing

Thankfully, we could do a rhetorical analysis of other websites in any given industry to see what the norm is, and we can follow up with clients and in focus groups to ask people what their response to website copy is. We don't have to trust a guru's gut (Not Trusting the Guru Gut will be the next book) about what's effective for any given purpose and audience.

If cute and funny end up winning the day in every industry, sector, and audience, so be it! I know, though, that if had asked my students about whether that was a sound rhetorical analysis, they'd have frowned.

Do Your Homework

So, instead of going to the copywriting service that this guru was recommending, which shall also go nameless here, you should find a copywriter who's got some knowledge of rhetoric or some very detailed knowledge about the audience you're trying to communicate with or the industry/sector that you're trying to reach. Finding just anyone and figuring out too late that that person thinks a blanket approach to writing website copy will do... Yeah, you don't want to find yourself in that position. It'll be an expensive bag to be left holding.

I promised myself that I'd only spend an hour on this post, because rapid rivers of ink have gushed forth from those smarter and more qualified than I to opine on the matter of the use of singular "they." But a friend and colleague asked the other day whether it's right or wrong to use the singular "they," so let's have that conversation.

Neither right nor wrong

As with most usage issues in English, it's not as if there's a definitively right or wrong way to use singular "they." I say that with my descriptivist hat on: I'm trying just to describe how English gets used, not lay down proscriptions about whether it should be used in this way or that. The "should" approach is called the prescriptivist approach. We'll get to that. But the upshot is that you'll never hear me or anyone from the Laughing Saint Editorial's crew say that singular "they" is right or wrong per se. We're going to talk about whether it's appropriate once we get into the prescriptive side of things later on.

So, what are you going to learn in this post? A little bit about what other experts say, a little about gender theory, and a little about yourself.

Please ignore Grammar Girl

I've got a post I'm saving up about why Grammar Girl isn't your friend (do you use WebMD instead of a doctor? No. So you shouldn't use Grammar Girl and assume you've gotten accurate grammar/usage advice. I digress). That said, we do need to start this conversation by looking at what experts (i.e., not Grammar Girl) have said about the use of singular "they," both descriptively and prescriptively.

I'm a rhetorician with a background in linguistics (my dissertation director was a nationally-recognized linguist who helped create the Dictionary of American Regional English, and I have something like a master's worth of coursework in English grammar, including English-language history and functional, cognitive, and generative grammars), which means I think of language/linguistics as the foundation of rhetoric. Rhetoric is, more or less, how we use communication--verbal and otherwise--to do things. Note the importance there of the word "use." "English language usage" refers to customs of language usage, not the rules (flexible and dynamic though they may be) of grammar, which is really about how words get put together to make sense (but whether they achieve some purpose, well, that's a question for rhetoric and usage and style rather than grammar). Grammar is how the Lego blocks fit together; rhetoric is whether you've used your blocks to make a castle or a bridge and why you'd want to build one or the other.

So, before we can understand whether and how to use (!) singular "they," we have to understand its basis in language and the history of the language. The fact is that singular "they" has been used in the English language since before "correct spelling" was a thing. There's something like four centuries of time lag between the two, actually: singular "they" is at least as old as the 14th century, and spelling and other matters of language use were being codified in the 18th and 19th centuries. That's just the descriptive facts. So the historical argument suggests that there's precedent both for using singular "they" and for not using it, as language standards started to be implemented.

Since history won't save you, how about the brain? Here's a great analysis from the Bible of approachable linguistics scholarly news, Language Log, about how using the singular "they" has been shown to require increased processing time (meaning: it does seem to take a handful of milliseconds longer to understand what "they" or "their" refers to when it refers to a singular noun). But we're talking about milliseconds, not a complete breakdown in semantics (how sentences make meaning). So cognitive arguments aren't going to save you, either, because it would be patently risible to claim that understanding singular "they" creates such a significant cognitive burden that singular "they" should never be used.

What about semantics, though? Can you argue that the use of singular "they" creates vagueness in sentences that can't be overcome? Actually, I think this is the best argument against using it. Note that the sentence "The student took their book to class" makes perfect sense to some folks. To me, it causes at least momentary confusion: Wait, did this person intend to use "their"? Are we suddenly talking about some other group of people? Did I miss the change in subject or meaning? Grammatically, we can change the rules (or change them back) such that "they" is officially alright to use in singular contexts, but just like I have to read some sentences a couple of times before I understand whether "read" is past or present tense, I might have to read a sentence that uses singular "they" a couple of times before I'm assured of whom we're talking about, and there might still be some ambiguity. Furthermore, at the moment, we don't allow for "themself," which would be the singular reflexive form of the plural pronoun, which suggests to me that we're still not there, descriptively, when it comes to the singular use of the plural pronoun. I could be asking for too much (we use "themselves" as the singular reflexive instead), but I think that when we get to "themself," we'll be fully in singular "they" semantics. Right now, we're not.

On the ground

That said, when it comes to language use on the ground, some folks use singular "they" to promote a gender-neutral perspective. In many ways, I support this, but that's not my only reason for using singular "they," though I don't use it all that often (see the semantic argument against it, above). That said, I do use singular "they" not only in speech but occasionally in my Oratoria posts and elsewhere. There are good reasons to use singular "they," just a few of which include:

Respecting other people's wishes when it comes to the pronouns they prefer. Don't be a self-righteous jerk: if someone asks that you use "she" or "they" or "he," just do your best to do that. There's no reason to make a big deal about it. If that person changes their (!) mind about it later (an argument I've heard against having to keep up with personal pronoun choices), what's it to you? You can be forgiven slip-ups, in that case, but remember that most of the time, making that kind of change isn't something an individual takes lightly, so don't plan on being asked to adjust more than once per person.
Accepting linguistic (and social) change. It's not so much that words change, but our use of and rules for them change. Happens all the time. Don't imagine that you've got the form of English that G-d loves best. Unless you've got some stone tablets lying about that you wanna tell us about, and those tablets are about grammar and usage, there's no reason to be upset about language change. Unless you're trying to use language as a tool of oppression or control, that is.
It fits the context you're writing or speaking for. If I'm editing a blog post written for a website geared to people in their teens, I'm giving a pass to singular "they." If I'm editing a book written by one of my clients in the business world, there shall be no singular "they" if I have anything to say about it. The Chicago Manual of Style is unequivocal about their rejection of singular "they" (I have to believe it's because it occasionally creates ambiguities that can't be resolved semantically/grammatically), for example. So is The New Yorker. As a rule, for me, I decide to allow singular "they" if and only if:
1. It doesn't create ambiguities that can't be resolved easily by the reader
2. The applicable style guide allows for it
3. The audience is likely not to have a fit about it
4. The writer wrote it (i.e., I won't go adding it where it isn't already).

So, it's not as if this is a right-or-wrong issue. It's really a matter of rhetoric: how do you plan to use singular "they," and why? Will it work in your specific context? Those are the salient questions.