5 punctuation problems even experts can't agree on

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's my recent column looking at five punctuation problems my experts couldn’t agree on.