conundrum

Noun

conundrum (plural conundrums or conundra)

1. A difficult question or riddle, especially one using a play on words in the answer.
   • “Why should I understand that, or anything else?” asked the girl. “Don’t bother my head by asking conundrums, I beg of you. Just let me discover myself in my own way.”1815 December (indicated as 1816), [Jane Austen], chapter 2, in Emma: […], volume (please specify |volume=I to III), London: […] [Charles Roworth and James Moyes] for John Murray, →OCLC
   • Besides assisting in unravelling these two etymological conundrums, the present research also made an effort to approach a greater accuracy in presenting the original sources of borrowed words.2018, James Lambert, “Anglo-Indian slang in dictionaries on historical principles”, in World Englishes, volume 37, page 255

   Synonyms:

   brain-teaser, enigma, puzzle, riddle, crux

2. A difficult choice or decision that must be made.
   • And while I am more concerned about the well-being of others than for myself, more hurt for them and for their losses than for my own, more worried for their futures than for the future of Martha Stewart the person, you are faced with a conundrum, a problem of monumental, to me, proportions.2004, Martha Stewart, statement read before being sentenced to five months in prison
   • Herb was initially overcome by Jakarta ('The impressions of noise, chaos, tremendous crowdedness and I suppose whitelessness were perhaps the strongest, and I felt something of a stranger') and faced with the familiar conundrum ('again the sensation of the thousands of hungry people all around –...2011, Jemma Purdey, From Vienna to Yogyakarta

   Synonyms:

   dilemma, Catch-22, Hobson's choice, Morton's fork, no-win situation, quandary, Sophie's choice