conundrum

Conundrum is one of English's great etymological orphans. It first appeared in the late sixteenth century, initially meaning a whim or a crotchet, then shifting to mean a pun or wordplay, and finally settling on its modern meaning: a confusing and difficult problem. The word's own origin is, fittingly, a conundrum.

The most popular theory is that conundrum is mock Latin — a pseudo-scholarly invention, perhaps coined by Oxford or Cambridge students as a parody of academic jargon. The '-um' ending mimics Latin neuter nouns (quorum, decorum, memorandum), and university students of the sixteenth century loved inventing absurd Latinate words to mock pedantry. If this theory is correct, conundrum is itself a joke about language.

Other theories are less satisfying. Some have linked it to the Latin conandrum (an attempt), or to an Irish or Welsh root, but none of these hold up to scrutiny. The Oxford English Dictionary simply marks the origin as unknown. For a word that means 'an insoluble puzzle,' the absence of a solution to its own etymology feels less like a failure and more like a feature.

The word gained its current meaning — a difficult problem with no easy answer — by the mid-seventeenth century. It shed its earlier associations with puns and wordplay and became serious. Politicians, philosophers, and newspaper columnists adopted it for problems that resist binary solutions: the conundrum of free will, the conundrum of nuclear deterrence, the conundrum of immigration.