Mine is a question involving grammar and preserving my sanity. I work for a very wealthy family who, rather than solely passing on genetic markers, pass on one particularly grievous grammatical error. It started with the matriarch of the family and was passed down to two of her daughters, followed by an employee of one of said daughters.

When asking me to do something, they start their inquiry with “may you please.” An example from today was a request to send a wire transfer, followed by “May you please let me know when this goes out?” I’ve gotten two “may you please” requests today and they frankly make me want to put my head through the wall, much like, but more effectively so than, Situation Sorrentino.

The employee sends me multiple email requests daily so my question is, do I just need to suck it up and deal, or is there a subtle way to tell her that this is not proper English? I realize saying that something to the matriarch or her daughters is a lost cause and could lead to a lost job, but I feel like it’s irresponsible of me to allow this to be passed on any further. Also, I feel like a little bit of me dies inside every time this happens. HELP!

May I please give a grammar smackdown?

Dear May,

It’s two issues, really: 1) is it wrong; and 2) if it is wrong, should you say so.

I would say it’s wrong. “Grievous” is a bit strong; the usage sounds like an overcorrection, in an attempt to sound more formal or courteous, or perhaps a regionalism in the vein of “might could” or “could do.” Googling the string “‘may you please’ incorrect” turns up a lot of proofreading requests from non-English speakers, interestingly. That may not apply here, but it seems like sometimes it’s a translation tic…vestigial code, kind of.

Would I correct it out of a document I’m copy-editing? Yes. Would I mention it in this case? No. Unless she’s using it in public-facing documents or correspondence, it’s likely not worth it to point it out, and even then, it is probably an attempt to seem more polite (not to mention that people see, and fail to register, felonies against the language on a daily basis), and not really something you need to get her out of her own way on.

I get that it’s annoying because you hear it all the time, but welcome to having a boss. If it weren’t this, it would be the weird clicky noises she makes when sealing an envelope, know what I’m saying? What I also get is something maybe you didn’t intend to tell me: that part of your irritation may stem from resentment of, and desire to feel superior to, the “very wealthy family.” This isn’t a judgment; resenting, and wish to feel superior to, all sorts of people is a founding principle of the internet, and also working is a hassle, so seethe away. My point is that their relative privilege isn’t pertinent to their grammar — but you brought it up anyway, so it’s significant to you somehow. And if it’s coming through to me, possibly it’s coming through to them. Something to keep an eye on, perhaps.

Short form: the usage is wrong; sharing that fact with the user will not improve your life.

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