Good legal writers follow accepted rules of usage and style. But they also know that punctuation and grammar blunders can destroy any goodwill they’ve created with their readers.

One mark of novice legal writing is the haphazard use of three related punctuation marks: the hyphen, the en dash, and the em dash.

It’s easy, though, to learn the basic rules that govern these marks. And if you learn to use them correctly, they will add clarity — even beauty — to your legal writing.

The Hyphen

The hyphen is the smallest of the three marks, and has several uses:

  1. Phrasal adjectives. A hyphen is generally required between two or more words that jointly modify the word that follows. These multiple-word modifiers are called phrasal adjectives or compound modifiers. So health-care professional needs a hyphen between health and care because the words jointly modify the noun professional. There are exceptions to the phrasal-adjective rule, which you can find here.
  2. Compound words. Hyphens are needed to form some compound words. Common examples are (a) numbers and fractions such as thirty-one and one-third; (b) nouns such as sister-in-law; and (c) titles and proper names such as ex-President and anti-American. In some cases, it will be unclear whether a compound word needs a hyphen because time has gradually fused the two words (e.g.decision-maker v. decisionmaker). If you’re unsure whether a compound word needs a hyphen, consult an up-to-date dictionary or usage manual.
  3. Words that are spelled alike but have different meanings. Examples of these words are re-cover/recover and pre-judicial/prejudicial. Depending on the meaning, a hyphen might or might not be needed.
  4. Compound words beginning with the prefixes self-, ex-, quasi-, and all-Examples of these words are self-confidence, ex-wife, quasi-tort, and all-powerful. But as Richard Wydick notes in Plain English for Lawyers, hyphens usually aren’t needed when the prefix is anti-, co-, de-, inter-, intra-, multi-, non-, para-, pro-, re-, semi-, or super-. Again, consult an up-to-date dictionary as the final arbiter.
  5. Words that fall on the end of a line. Some word-processing programs can automatically hyphenate words at the end of a line. If you don’t select automatic hyphenation, however, the program will automatically move the whole word to the next line. If you use automatic hyphenation, make sure that the program inserts hyphens between syllables.

The En Dash

An en dash is larger than a hyphen and about one-half the size of an em dash. In Typography for Lawyers, Matthew Butterick points out that writers can use en dashes to “indicate a range of values” or to show “a connection or contrast between pairs of words.”

  1. Range of values. The en dash replaces the connector to in ranges in dates, paragraphs, and pages. Instead of writing 1933 to 1940, pages 31 to 45, and paragraphs 10 to 15, insert en dashes to make these ranges 1933–1940pages 31–45, and paragraphs 10–15. In legal memoranda, en dashes indicate that a citation spans multiple pages in the source material. For example, an en dash — not a hyphen — is needed in this pinpoint case citation: Unites States v. Brown, 123 F.3d 456, 465–70 (2013).
  2. Connecting or contrasting pairs of words. Butterick also points out that en dashes are needed to connect pairs of words such as conservative–liberal split, Arizona–Nevada reciprocity, and Sarbanes–Oxley Act.

The Em Dash

The em dash is the largest of the three marks — it’s approximately the width of a capital M. The em dash is also the most versatile but underused of the three marks in legal writing. It’s a shame that the em dash has fallen into disrepute among lawyers, because an adroitly placed em dash can make even ponderous legal writing digestible.

In Writing with Style, John Trimble explains that some writers avoid em dashes like the plague because

the dash is so versatile and so eager to work [young writers] will work it silly, asking it to double as a comma, a semi-colon, a parenthesis, a period, ad scandalam. This is why it’s tagged as a mark of Easy Virtue by many staid writers, especially lawyers, who rarely let it near their prose. Such an overreaction is a pity, because when the dash errs, it’s a victim, not a culprit, and nothing can quite replace it. In fact, of all the punctuation marks, it’s the most indispensable for brightening our prose.

Trimble says that the em dash can do five things quite well, and gives some actual examples of its use:

  1. Inserting an interruption or break in thought: “Life without romance—well, you might as well be in prison or a slug under the earth.” Charlie Chaplin
  2. Serving as a conversational colon or light bridge: “That’s the worst of facts—they do cramp a fellow’s style.” C.S. Lewis
  3. Isolating a concluding phrase for emphasis or comic effect: “I could never learn to like her—except on a raft at sea with no other provisions in sight.” Mark Twain
  4. Inserting a parenthetical explanation, qualification, or amplification: “Easter weekend arrived, and our cherry trees—about thirty of them—blossomed in unison.” Peter Mayle
  5. Marking a collection of several ideas: “The art of the surprise witness, the withering cross-examination, the sudden objection phrased in arcane formulas—all seem to bespeak a profession based on elaborate training and requiring consummate skill.” Time

In legal writing, em dashes are particularly useful to set off a parenthetical where inserting commas would be too weak for the job or would clog the sentence, and where unsightly parentheses would jar the reader by requiring him to stop mid-sentence.

Consider the following sentences:

  • John Taylor, who’s known for his blunt oral-argument style, dazzled the courtroom. (The commas deflate the parenthetical, which is crucial to the idea being conveyed by the sentence)
  • John Taylor (who’s known for his blunt oral-argument style) dazzled the courtroom. (The parentheses stop the reader mid-sentence)
  • John Taylor – who’s known for his blunt oral-argument style – dazzled the courtroom. (The hyphens are plainly wrong)
  • John Taylor — who’s known for his blunt oral-argument style — dazzled the courtroom. (The em dashes strike the right balance by emphasizing the lawyer’s “blunt oral-argument style” without bringing the reader to a full-stop like the second example)

You can set em dashes flush with the surrounding text or add spaces before and after the dash as I’ve done here. Depending on the font, the extra spaces can enhance readability, and the spaces can also prevent awkward breaks at the end of a line. But whatever you choose to do, be consistent.

Professional Writers Care About Punctuation and Grammar

Yesterday, another Lawyerist contributor flippantly claimed that certain unnamed punctuation and grammar rules are “more like guidelines,” which lawyers can discard when it suits their personal predilections or when it’s necessary to placate the whims of ill-informed colleagues.

But as Rudolf Flesch writes, hewing to accepted rules of punctuation and grammar is indispensable to making readers’ lives easier:

Punctuation, to most people, is a set of arbitrary and rather silly rules you find in printers’ style books and in the back pages of school grammars. Few people realize that it is the most important single device for making things easier to read.

Richard Wydick had this to say about the subject: Disregarding generally accepted punctuation and grammar rules “is an abdication of the professional duty to express meaning as clearly as possible.”

Or, how about Bryan Garner:

Where punctuation is merely wrong, and the meaning unaffected, the discriminating reader draws other types of inferences—usually unfavorable ones—about the writer. Any writer wants to avoid these, for they commonly extend beyond one’s grammatical knowledge to one’s level of education and carefulness in general. Well-crafted writing lends credibility to what is being said . . . We cannot divorce style from substance.

(adapted from Litigation (Summer 1989)).

In other words, a loose attitude towards proper punctuation and grammar in your legal writing can make you look foolish and risks disserving the interests of clients who pay you to follow the generally accepted rules.

If you believe that lawyers should aspire to be professional writers, take some time to learn the basic rules of punctuation and grammar, including the rules above for hyphens, en dashes, and em dashes. Clients don’t expect you to take a willy-nilly approach to their matters, so don’t take a willy-nilly approach to these marks in your writing.