(ChatGPT wouldn’t let me generate an image for the “sexy pet store owner” example.)
In formal publishing, editors guard the distinctions between punctuation marks carefully, and the rules for when to use hyphens can seem especially fussy. For example, the Chicago Manual of Style suggests a hyphen for Winston-Salem, but an en dash for Epstein–Barr virus.
The Associated Press Stylebook has steadily pared back its usage of hyphens. See the “Punctuation” section on this page for some riveting discussion. Their guidelines used to say that you should put a hyphen in pre-eminent, but as of last year, they advocate preeminent. (By way of protest, I now hear the word in my head with three syllables—PREE-mah-nent—whenever I see it spelled that way.)
The general rule is to use hyphens when leaving them out would make a sentence ambiguous, incorrect, or difficult to pronounce. Words routinely “graduate” from hyphenated to unhyphenated once they become familiar, so in some sense AP just did a mass graduation ceremony with their revised style guidelines. Today was once spelled to-day, and only by the 20th century (1920s in the US, and 1950s in the UK) did the fused spelling become the convention. On-line and e-mail are more recent examples. Using either of these hyphenations could mark you as a Gen Xer or worse. (Come to think of it, “online” sounds boomerish in 2025 with any spelling. Isn’t everything online now?)
Hyper-hyphenation
Speaking of being online, I ran across a BlueSky thread asking if there are any 4-word hyphenated adjectives. Answer: Yes, many. But this had me wondering about the most hyphenated naturally-occurring word.
Terms with 2 hyphens (mother-in-law, over-the-counter) and 3 hyphens (jack-in-the-box, middle-of-the-road) are fairly common, but it starts to get weird after that.
Using OneLook’s wildcard features we can find words that have 4 or more hyphens pretty easily by searching for *-*-*-*-*, which means “find 4 hyphens surrounded by other stuff.”
This search returns many longwinded chemical compounds—boring!—but also a few adjective phrases that you might call hyper-hyphenated, such as what-you-see-is-what-you-get and knock-down-and-drag-out.
The sole non-chemical noun phrase with 5 or more parts is this tall and enticing plant called kiss-me-over-the-garden-gate.