4.3 Minor Markdown Variations ↑

4.3.1 Curly Apostrophes

Curly apostrophes, otherwise known as “smart” apostrophes, offer some surprisingly devilish choices, when it comes to implementation by a Markdown parser.

To start with, John Gruber’s original write-up on his SmartyPants project makes the following notes about apostrophes:

• First, there is no explicit mention of apostrophes in describing the intentions of his project; they initially appear to be just lumped in with the topic of curly quotes.

• Second, he offers some sympathy for users who really don’t care whether the apostrophe in “Joe’s” appears as straight or curly.

• Third, he notes that, even for those who do care, converting normal ASCII characters to HTML entities may make it more difficult for others wanting to copy and paste text.

• Fourth, he notes some algorithmic shortcomings: cases in which it is just close to impossible for a parser to figure out whether a single quote character should be made curly.

But even when one wishes to identify a single quote character as an apostrophe, there is some ambiguity built into HTML itself: namely, there is a specific HTML entity hamed &apost;, which is provided to express the intention to display an apostrophe, but this entity reliably renders as simply a straight apostrophe, without any curliness; so if one wishes to show a curly apostrophe, one actually has to request a right single quote character.

This discussion concerning straight and curly quotes from Buttericks’s Practical Typography also notes that: “If you’re tempted to write your own straight-to-curly converter, reconsider — the good ones cover tricky edge cases that you’re apt to miss on your own.”

So, taking all of this into consideration, the Notenik Markdown parser now defaults to curly apostrophes (starting with Version 9.0.0), but provides an option, on the Collection Settings screen, to turn this off, in case it is producing results that seem less than useful in a particular context.

If there are edge cases I’m missing, I’m also always open to further user feedback on this topic.