It’s a pleasure to return to Overthinking It with a post in the Grammar Thursday series. Why grammar? Because I’m an obsessive nitpicker. Why Thursday? Couldn’t say. Enjoy.

A bunch of the Overthinkers graduated college around the same time, and we’re coming up on a few summers full of tenth anniversaries. So we’re getting a bunch of “save the date” cards, at the top of which is emblazoned something like this:

What’s wrong here? Where to start?

The apostrophe is a mark of punctuation used to denote contraction or elision, the shortening of words or groups of words. Some of these make sense intuitively, like “didn’t”, some of them don’t, like “ain’t”, and some of them have passed out of common use, like “’tis.” (Look at the direction of the quotation marks and apostrophe.)

Apostrophes are notionally different from the closing single quotation (what the English call “inverted commas” and which they use to demarcate speech), though you wouldn’t be able to tell them apart at sight. Typefaces usually don’t have distinct characters characters for them. Computer keyboards use one button for both. But the apostrophe stands on its own where as the single quotation mark needs a mate.

So, when “Class of 2002” is shortened to “Class of ’02”, it’s self-evident the proper mark of punctuation to use is the apostrophe, not the opening single quotation mark, which hangs forlornly, as though peeking over the numbers to find a mate that will never come.

“Smart” quotes, a feature of many word processors (and the blogging software that runs Overthinking It) intended to make your documents look typeset instead of merely typed, is usually implemented with an algorithm that assumes that if an apostrophe follows a space, it’s intended to open a quotation, and that when it follows a letter or mark of punctuation, it’s meant to close one. Reasonable enough, I guess, except that in the United States, we use double quotation marks except when you’re nesting quotations one inside another. Which rarely happens outside of college creative writing seminars.

While we’re complaining about marks of punctuation, here are a few other ways you can get it wrong.

This character is called a single prime. It’s used to denote measurements of length in feet, and arc-minutes (as in our constant appeal for the ICBM Address of anyone who writes into the Overthinking It Podcast). It’s not an apostrophe.

Computer programmers usually call this mark a “backtick,” and it’s used for setting of certain kinds of data (table names in an SQL query, for example). It shouldn’t be confused with any of the other marks we’ve mentioned, and shouldn’t be used in place of an opening single quotation mark.

We’re getting closer. The character above, a “dumb” apostrophe (like on a typewriter, which couldn’t dynamically change the characters you type based on context), is at least not technically wrong. But it can be improved upon:

Ahhh. Don’t you feel better? I do!

PRO TIP: If you want to make sure your apostrophe is an apostrophe, you can type Option-} on a Mac. But if you’re stuck in Microsoft Word and don’t want to deal remembering four-digit codes that you have to type on numeric keypad, you can use this little hack.

To start a word with an apostrophe, type two apostrophes in a row. The software will interpret the first one as an opening quote and the second as a close quote, thus: ‘’. Finish typing the word and the space after it (since some auto-correct algorithms activate at every word-boundary and could undo all your hard work), thus ‘’tis . Go back and delete the opening quotation mark, and you’re typographically set.

Care to “Well, actually…” me? Want to dazzle the readership with your superior grasp of grammar? Or to point out that this post isn’t about grammar at all? Join the pedantic pissing contest in the comments!

Oh, and here’s that typeface. Boola boola.