conundrum
UK: kəˈnʌn.drəm | US: kəˈnʌn.drəm
n. a confusing and difficult problem or question
n. a riddle or puzzle, often involving a play on words
The word "conundrum" likely originated in the late 16th century as a mock-Latin term, possibly coined at Oxford University. Its components suggest a sense of "tangled" or "confused" ideas (con- "together" + undr- "wave," implying something that fluctuates or is hard to pin down). Over time, it evolved to specifically denote riddles or complex puzzles, especially those relying on wordplay.
The detective faced a conundrum: all suspects had alibis.
She loves solving conundrums in crossword puzzles.
The ethical conundrum left the committee divided.
His riddle was a clever conundrum involving homonyms.
Modern technology presents new conundrums about privacy.