A Word, Please: Sometimes punctuation rules come up short

It's better to put the quotation mark after the S in “Casablanca’s” best scene, grammar columnist June Casagrande writes.
Ingrid Bergman and Humphrey Bogart in a scene from “Casablanca.” It’s better to put the quotation mark after the S in “Casablanca’s” best scene, grammar columnist June Casagrande writes.
(File Photo)

A few years back I set out to write a comprehensive punctuation book — one that laid out the rules for proper punctuation in every situation imaginable.

How naïve I was.

You don’t have to spend a lot of time digging through reference books to know that in some situations, there are no rules. For example, do you put a comma in “What it is is a new house”? Where do you put the apostrophe and S in “Casablanca’s” best scene? How many hyphens do you put in “30-day-dry-aged beef”? Would you hyphenate “You can donate tax-free”?

The Associated Press Stylebook and the Chicago Manual of Style lay out lots of basic punctuation rules. But in certain gray areas, they’re useless. Lots of academic books and professional style guides have basic rules, but they’re no help in tough punctuation situations.

I had an idea: Why not survey a few working editors to ask what they would do? That way, for situations with no clear rules, readers of “The Best Punctuation Book Period” could benefit from experts’ own best guesses.

The editors who took my punctuation survey disagreed on how to handle some tricky situations. Here are five punctuation problems my experts couldn’t agree on.

1. What it is is a good idea. Two of the editors I surveyed said to insert a comma after the first “is.” Two said don’t. So you can choose either way. My two cents: It’s wrong to insert a comma between a subject and a verb: “The dog, is a schnauzer.” Seems to me the same logic should apply even if your subject is “what it is” and your verb is “is.” So I’m anti-comma here.

2. “Casablanca’s” best scene. In some editing styles, you put movie and book titles in italics. In others, they go in quotation marks. So when you’re using quotation marks style, how do you make the title possessive? If you put the apostrophe and S inside the quotation marks, you’re suggesting they’re part of the movie title. If you don’t, it looks terrible: “Casablanca”’s best scene. Some members of my Punctuation Panel said to put the possessive marker inside the quotes, others said keep it outside. As for me, I got it in my head years ago that aesthetics trump logic in this case. So I vote for “Casablanca’s” best scene.

Casual readers may not notice grammar mistakes, word choice errors and reader-unfriendly language that drive editors to distraction.

3. 30-day-dry-aged beef. The reason you hyphenate compound adjectives is to show how different words relate to the noun. In a “small-business conference,” the hyphen tells you that the businesses, not the conference, are small. That’s why I vote for three hyphens in our beef example. This isn’t 30-day beef that’s dry-aged. All four words form a single modifier. Half my Punctuation Panel agreed. The other half preferred “30-day dry-aged beef” with two hyphens instead of three.

4. What Jones lacks in age she makes up for in intelligence. Three out of four Punctuation Panel members said no comma after “age.” I agree. When you parse the syntax of this sentence, you see that “what Jones lacks in age” is actually the object of the preposition “for.” Rearranged, it means: She makes up for what she lacks. A comma doesn’t belong between a preposition and its object: “I picked flowers for you,” not “for, you.” But when the object is a long phrase that’s moved to the head of the sentence, “What Jones lacks in age,” it’s structured more like an introductory clause — a unit that’s often followed by a comma. Hence the panel’s disagreement.

5. You can donate tax-free. Style guides give a lot of advice on how to hyphenate compounds when they modify a noun like “donation” in “a tax-free donation.” The rule is to hyphenate whenever it helps the reader understand the relationships between the words. But there are no rules telling you what to do when the compound is describing not a noun but a verb. The Punctuation Panel split on “tax-free”/“tax free” as an adverb. You can choose whichever way you think is clearer. My two cents: I say you donate “tax-free.”

June Casagrande is the author of “The Best Punctuation Book, Period.” She can be reached at