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A hyphen (-) connects two things that are intimately related, like toll-free or three-fourths. An en-dash connects things related by distance. For instance, The park is open from May-September, or For homework, the teacher told us us to read pps. 137-228. An m-dash is often used in lieu of a comma, as a way of interjecting a clause to better explain something — like this, which shows how an em-dash can be used. You’ll often see m-dashes rendered as two n-dashes placed consecutively, like this --. They can be easier to read, especially online.
Technically, there exist three lengths of what are all more or less dashes: hyphen (-), en-dash (–), and em-dash (—), but most people (and most word processing programs) stick with two: the en-dash, which also functions as a hyphen, and the em-dash, which is longer — because “m” is wider than “n,” get it? In Wordpress and Microsoft Word, if you put in a dash, you get a hyphen and/or an en-dash; if you input two hyphens together (--), they automatically convert them into an em-dash (—). (Source: Chicago Manual of Style)
A compound adjective consists of two words that, when put together, comprise a single adjective. They require a hyphen. Free-range chickens, a five-page story, or a remote-control car, for instance. The hyphen implies that the two words are linked, since neither can do the work on its own. “Free chickens” would only make sense if you were not charging for them, and there is no such thing as “range chickens.” Neither does a “five paper” or a “page” paper. At best, a “remote car” could imply that it was parked at a distance, while the meaning of a “control car” is unclear.
Compound adjectives promote clarity. “He saw a man-eating alligator” isn’t the same as “He saw a man eating alligator.” In the first, the alligator eats people; in the second, the guy might be munching on alligator meat. (I hear it tastes like chicken.)
Some examples:
I bought an eight-foot table.
She works in a 60-story skyscraper in midtown.
We ate almond-crusted sole for dinner.
Sheryl is a well-known musician.
Harry is studying in a well-lit classroom.
He is in a long-term relationship.
Would you grill the pork chops with that world-famous recipe of yours, please?
You hyphenate the two adjectives when they modify a word, but you don’t if they are used elsewhere in a sentence.
She is a part-time employee at her local McDonald’s.
She works part time at her local McDonald’s.
He published a 300-page book on the love life of lizards.
He published a book on the love life of lizards that is 300 pages long.
We made a last-minute decision not to go to the game.
We made a decision at the last minute not to go to the game.
A fire-proof vest wouldn’t be a bad idea for Santa Claus.
Santa’s vest is fire proof.
Whenever the word “well” rears its head as part of an adjective, you use a hyphen.
A well-written novel.
A well-received play.
A well-regarded member of the community.
You also deploy a hyphen when you have adjective/adverb/noun and present participle (-ing words):
That’s a fine-looking cat you have there.
Her team had a record-shattering run in the 400 meter relay.
This is a mouth-watering meal.
She is a forward-thinking journalist.
I seek a time-saving method for learning English grammar and punctuation.
Same with the past participle (-ed):
His are old-fashioned ideas.
The detectives are investigating a cold-blooded murder.
I am in the market for a wind-powered generator for my country house.
Just because two adjectives sit next to each other and modify a noun doesn’t necessarily mean that you hyphenate them. They have to work together to earn that hyphen. You would not bother if they describe different aspects of the same noun.
A big, blue book sat on our coffee table. (The book is blue; it is also big. Each adjective can function without the other.)
I just returned from a nice, relaxing vacation. (The vacation was both nice and relaxing.)
They live in a comfortable, spacious house by a lake. (Their home is both spacious and comfortable.)
You also do not hyphenate two descriptor words if one of them is an adverb (which describes a verb).
That is a beautifully painted portrait and should be on display in a museum.
She is an extremely smart student who outworks her classmates. (You go, girl!)
He would be an easily misled target because he is so gullible.
An exception -- you knew that was coming, didn’t you? -- arises when an adverb could also be an adjective, such as “well” and “fast.” These are known as “ambiguous adverbs” (which sounds a bit like the name of an indie rock band).
She aimed her bow and arrow at a fast-moving target. (The target can be both fast and moving. Normally you would not hyphenate them, as we discussed above. You would write it fast, moving target. But here, you do.)
The company touted its fast-growing seeds. (You see the word fast in front of a word that describes a noun, hyphenate it. Same goes with its opposite: slow, as in slow-growing seeds.)
I bought a pair of well-worn jeans second hand at a thrift store. (“Well” describes “worn,” which is an adverb. But with the word “well” you hyphenate.)
A well-fatted calf plays an important role in the Bible. (Same idea.)
If the descriptor happens to be a proper noun (meaning the name of something), then you don’t use a hyphen.
I feel sorry for you if you purchased New York Jets tickets for the upcoming game.
I just bought the latest Rolling Stones album.
And you can also have compound adjectives longer than two words.
Mabel stole candy from a three-year-old boy.
She and her son were playing that ring-around-the-rosy-pocket-full-of-posey song.
I need a quarter-of-an-inch-thick piece of cloth.
In the corner of the store window stood a five-foot-ten-inch tall mannequin.
My teacher assigned a lot of fill-in-the-blank-type quizzes over the course of the year.
You can, in addition, have two separate words that are hyphenated in a sentence, which can be a little tricky.
Last summer, I took a large group of eight- to ten-year-old boys on a picnic in Washington Square Park. (The ‘to’ breaks up the compound adjective, so the hyphen comes before, followed by a space, the ‘to,’ then the rest of the compound adjective.)
I am looking for a dozen three-to-five-inch-tall and one-to-two-inch-wide antique figurines to add to my collection.
Finally, you can have two (or more) compound adjectives in a sentence.
We caught a twelve-pound, thirty-two-inch-long striped bass from our yacht.
One last point: separate from compound adjectives are compound words, which also require hyphens. Words like fact-check, editor-in-chief, mother-in-law, father-in-law, five-year-old, six-pack (or twelve-pack), and factory-made.
You should always fact-check your work.
I have two kids: an 11-year-old and a 9-year-old.
The editor-in-chief killed my story.
Those pastries were factory-made and not fresh from a bakery.
She brought a six-pack of beer to the party.
Whew! It probably seems complicated, but it's not, really, once you get the hang of it.