Unscrewing the inscrutable.

Dear Word Detective: I’ve got quite the “conundrum” for you. What is the origin of this very obscure word? It has at least three synonyms that I know of (riddle, puzzle, enigma), so I don’t imagine it’s the first of these four to mean what it means. The online dictionary explained its meaning quite well, but nothing about its origin, and a search simply yielded countless “conundrums” that other people had. Please help. — Neil, Vancouver, BC, Canada.

Hey, you’re right. Googling “conundrum” produces 5,510,000 hits, and not a single one of them explains the origin of the word. I had to check each link, of course, because I wouldn’t be able to sleep if I didn’t follow every clue. Anybody know a good ophthalmologist? By the way, speaking of puzzles, I’m not sure I understand the second sentence of your question, so we’ll just skip that part.

The American Heritage Dictionary defines “conundrum” as “a paradoxical, insoluble, or difficult problem; a dilemma,” which covers a lot of ground. In any case, “conundrums” are generally not good things. A choice between your two favorite flavors of ice cream is not a conundrum; a choice between paying your rent or buying food is a conundrum. But it’s difficult to imagine remembering to use the word “conundrum” in such a dire situation, because “conundrum” is the sort of fancy locution, like the word “eschew,” that I seriously doubt anyone uses without careful forethought. Real people generally don’t say “conundrum.” They say “jam” or “pickle.”

Ask the folks at Oxford English Dictionary for the etymology of “conundrum,” and the answer is a terse “Origin lost,” as if it had been misplaced in a word warehouse on the outskirts of the city. The truth is more likely “origin never exactly known.” The most reasonable theory is that “conundrum” originated as a joke among university students in 16th century England, probably concocted as a pseudo-Latin nonsense word and initially used as a derogatory term for a fussy, pedantic and silly person (what the Oxford dictionary calls a “crotchet-monger”). Over the next two hundred years, “conundrum” was used to mean “a whim or silly idea” and “a pun” before it took on the sense of “a riddle the answer to which is a pun” in the late 18th century, and, soon thereafter, acquired its modern sense of “an insoluble or very difficult problem.” So the answer, unsatisfying as it may be, is that the birthplace of “conundrum” was probably just the warped imagination of a 16th century college student.

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