1. a difficult problem that seems to have no solution
2. a question asked as a trick that is answered by using words in a surprising way
Origin and usage
The noun conundrum looks like a Latin word but its origins are unknown. It was first recorded in the late 16th century as a term of abuse for a pedant, a meaning that is now obsolete.
These days a conundrum is most frequently a problem that seems to have no solution; this meaning has been used since the early 19th century. The other current meaning, of a riddle with a punning answer, is slightly earlier, dating from the late 18th century. In the two centuries that intervened between the first recorded use of the word and the appearance of the meanings above, conundrum had a few other meanings that have since disappeared. Verb collocates of conundrum include unravel, untangle and solve, while adjective collocates include bizarre, vexing, unsolvable and age-old. My favourite, though, has to be chicken-and-egg, an allusion to the unanswerable question: Which came first, the chicken or the egg? Conundrum was the title given to her memoir of transitioning from male to female by the writer Jan Morris, who died last week at the age of 94.
“There remains a chicken-and-egg conundrum: Did the show satisfy the cravings of society or did cravings lead to the shows?”
“He faces the moral conundrum of following orders or doing what’s best for the people he cares about.”
poser, riddle, trick question