by Arwen O'Reilly Griffith
Hyphenating compound words is a very tricky subject, and I thought it was time to tackle it. In fact, Wikipedia claims that "a definitive collection of hyphen rules does not exist," so we must muddle along as best we can.
Basically, the story is this: Hyphenating words is meant to clear up misunderstanding or ambiguity. When there are two or more words that express a single concept when combined, they should be linked by a hyphen. These are called "compound modifiers" because the first word(s) modify the second (or third, etc.) word.
The general rule requires hyphenating when a compound modifier appears before a noun. Examples: "well-sharpened saw," "ten-pound weights," "light-green toolbox." As you can see, without the hyphen, you might think that there were ten weights that weighed a pound each instead of a group of weights weighing ten pounds each, or that the green toolbox was not heavy, instead of being pale green. A hint from The Tongue Untied: if you can put "and" between the modifiers and it makes sense, you probably do not need a hyphen.
Just to make it even more complicated, please note: never hyphenate a compound word if it is an adverb ending in -ly. I don't know why this is, and couldn't find a concrete explanation for the life of me, but it must be so because Keith Hammond, MAKE's almost-infallible copy editor (note that clever use of a hyphenated compound word? Practically performative, this tip is!), says that it is. Also because I've seen it mentioned on many grammatical websites, sans explanation. (Whew! I think I came very nearly close to breaking a number of rules in that last sentence.)
Anyway, if you would like to know more, English Plus has a nice, wordy description about the history of hyphenation. Betcha didn't know such a topic existed, huh?
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