Minding Your aPostrophes and Quotation Marks

In the old days of writing with a typewriter, there was no option to distinguish between an apostrophe ( ’ ) and a single quotation mark ( ‘ )—they were typed with the same key that produced the same character meant for both situations: ( ' ).

The only people who had to worry about distinguishing between them were professional typesetters, and they knew what they were doing.

But then along came Microsoft Word and other word processing software, which offered the user the option to choose to add “typographer’s quotes” (sometimes called “smart quotes” or “curly quotes”) automatically. What this meant was that you could type "quotes" and it would render what you’d typed as “quotes.” If you wrote you're, it’d render it as you’re. This was a pretty nice feature.

But as with all simple fixes, it often failed to perceive important distinctions between the two punctuation marks. And so, there are an awful lot of single quotation marks out there where apostrophes should be.

So, what? you may be wondering. The problem is that these two punctuation marks have very different functions.

How to Use Quotation Marks

The quotation mark is one of the more intuitive punctuation marks to use. You place quotation marks around quoted material:

(1) Xinwei said, “I can’t wait until the next World Cup.”

You can also use them to signify that the word or phrase you’re using is so-called, that is, it’s what other people are saying but not what you would. Often, quotation marks can be used for ironic effect—an effect that has even carried over into speech with the use of air quotes.

(2) The locals like to order “hoagies,” by which they mean submarine sandwiches.

(3) Oh, yes, that real-estate magnate’s holiday letter was just so “classy.”

Single quotation marks are used just as the regular double quotation marks, but inside another quote.1Note that in the UK, this rule is exactly backward. Single quotation marks are used for the main quote, and double quotation marks are used for the embedded quote.

(4) Julia responded, “I don’t know what to tell you. He said, ‘I’m never coming back.’”

How Quotation Marks are Not Used


Quotation marks—either single or double—are not meant to be used for emphasis. If you want to emphasize something, use italics, bold, or underlining; don’t use quotation marks. I have seen some really bad examples, all of which call into question the very thing that the sign-maker or writer intends to emphasize:

  • You must have proper “ID” to enter. (Does this mean a note from my mother is okay?)
  • This machine does not accept “pennies” (Is that a slang word for that coin? What’s the right word?)
  • Our sandwiches are guaranteed “fresh”! (I don’t want to know what they really are.)


By virtue of the “smart quote” or “typographer’s quote” setting, single quotes are often used to make abbreviations. That role, however, is where the apostrophe comes in.

The Apostrophe

The apostrophe has three basic uses in English writing: marking an omission, the possessive, and making rare plurals.*

Marking an Omission

The apostrophe is used to mark a missing letter or letters, often in contractions:

  • didn’t—the contraction of did not
  • o’clock—an abbreviation of of the clock
  • rock ’n’ roll—an abbreviation of rock and roll

The last example leads us to one of the problems with modern word processors: when an apostrophe should come at the beginning of a word, the software will often automatically insert a single left quote ( ‘ ) instead. The following cases should all use apostrophes, not single quotes:

  • I’ve been a fan of theirs since the ’70s.
  • You can do this! Go get ’em!
  • ’Tis the season to be jolly!


One of the most common uses of the apostrophe is in marking possession. Even here, it’s really just marking the absence of a letter, the letter e from the original Anglo-Saxon genitive –es.

  • Bob’s new car
  • the chef’s apron
  • the chefs’ aprons
  • Briscoe and Logan’s investigation


I write this with fear and trembling, but in certain cases, an apostrophe can even be used to form plurals. However, it can only be used in those circumstances where not using some kind of mark would create confusion.

  • Don’t forget to dot your i’s. (to avoid confusion with the word is)
  • Many international students of English have difficulties pronouncing their the’s and that’s.

Now, I mention this rule with “fear and trembling” because of the frequent misuse of apostrophes to make plurals. Often referred to as the “Greengrocer’s Apostrophe,” it is the scourge of internet writing and roadside farm stands:

  • Fresh tomato’s, 5 for $2
  • We can repair your ski’s
  • I don’t know why they can’t speak English like real American’s

The Greengrocer’s Apostrophe is especially common on hand-painted house signs. On my house growing up, we had a lovely hand-painted sign that read:

The Schaefer’s

The Schaefer’s what? House? And which Schaefer owned it, exactly? Correct use of the apostrophe would have required either putting it at the end—The Schaefers’ [house]—or dropping it altogether: The Schaefers.

Minding Your P’s and Q’s

The apostrophe and the quotation mark are two of the smallest punctuation marks in English, and a person could be forgiven for thinking that I’m making too big a deal about which one is used where. Perhaps.

But proper punctuation, like many rules of style and usage, is often a sign of careful writing. A writer who pays attention to correct spelling and punctuation is more likely to pay attention to the bigger details of clear writing. Moreover, paying attention to the rules of punctuation is a way of signalling to your reader that you take writing seriously, you take your readers seriously, and you respect them enough to take your time and get your writing in the best shape it could be.

Plus, you get to avoid the grammatical scorn of obnoxious jerks on Twitter like this:

*I am placing an asterisk next to this rule to warn all to tread carefully when using it.