One of my absolute favorite sections of The Chicago Manual of Style (CMS) is section 7.77, entitled “To Hyphenate or Not to Hyphenate.” It’s a quandary that almost every writer encounters at some point, yet very few people are clear on all the many rules surrounding the shortest dash on their computer keyboard. That’s why I’m here—to help you make sense of where to place this punctuation mark on your page and when it's best for you to leave white space alone.

For part one of our hyphenation how-to, I’m going to talk about three parts of speech where hyphens do belong:

1) In verbal phrases used as nouns

When a verbal phrase that contains a verb and a preposition (“catch up,” “make out,” “stand in,” etc.) is used as a noun, it’s often hyphenated—e.g., “We’re due for a good catch-up,” “We had a serious make-out session,” “He was a stand-in for the lead actor.” Not all such phrases are hyphenated—for instance, “take out” is closed as “take out”—but, as you’ve heard from me before, use Merriam-Webster’s Collegiate Dictionary (www.m-w.com) to confirm what the correct format is.

2) In compound modifiers

This is a topic worthy of several posts on its own, because it requires a certain amount of practice and intuition to master, but the basic purpose of hyphens in compound modifiers, also known as phrasal adjectives, is to provide clarity about language that the reader might otherwise misinterpret. This happens most often when a compound modifier precedes the noun it’s meant to modify. The example I always think of is “small business owner”; when the phrase is open, you might think I’m describing the owner of a small business, but you might also mistake it as referring to a business owner who’s a small person. The way to avoid any such ambiguity is simply to hyphenate: “small-business owner.” The same goes for “much-needed rest,” “one-year lease,” “twentieth-century art,” “over-the-counter medicine,” “three-year-old boy” . . . and the list goes on and on. For a much more extensive summary of this subject, refer to CMS, chapter 7.

3) In single words that need a hyphen for clarity

Sometimes a single hyphen can change the entire meaning of a word. For example, “recreate” refers to leisure activities, but “re-create” means “create anew,” and “recollect” means “remember,” whereas “re-collect” means “collect again.” Similarly, “coop” probably makes you think of a place where chickens hang out, but throw a hyphen in there, and it becomes “co-op,” shorthand for a worker-owned organization.

Next time, I’ll introduce you to all the wonderful ways in which the need for hyphens has become nonexistent. (See how there’s no hyphen after “non-” there? That's just a taste of what's to come.) Until then, try dashing off a few sentences of your own, based on what you’ve learned today.

Have a grammar question? Leave it in the comments below.