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conundrum

/kəˈnʌndrəm/

A difficult problem, puzzle, or bewildering choice

From English, origin uncertain conundrum (A difficult puzzle or problem).

noun
conundrum
Late 16th-century English
conundrum
First recorded in the 1590s as an abusive term, perhaps for a pedant.
17th-century English/Oxford slang
conundrum; quonundrum
Used for a whim and for a mock-scholarly or punning expression.
18th-century English
conundrum
By 1745, a riddle built around an odd resemblance, often with a punning answer.
Modern English
conundrum

Conundrum entered English in the 1590s wearing what looks like a scholarly costume, but nobody can quite identify the tailor. It may have been an Oxford University joke: a pompous, mock-Latin word used to tease a pedant, much like hocus-pocus or panjandrum. One older theory connects it with Latin *conandrum*, “a thing to be attempted,” while Anatoly Liberman has proposed a link to the sixteenth-century Conimbricenses, Jesuit commentaries from Coimbra notorious for elaborate arguments about the many meanings of words. By 1745, the word had become a kind of verbal trap—a riddle whose answer depended on a pun or a bizarre comparison, such as a sash window being like a woman in labor because it was “full of panes.” Today it can describe either a brain-teaser or an agonizing choice, so a conundrum is not merely a question: it is a question that has somehow learned to smirk.

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