conundrum

noun

co·​nun·​drum kə-ˈnən-drəm 

1

a

: an intricate and difficult problem

He is faced with the conundrum of trying to find a job without having experience.

b

: a question or problem having only a conjectural answer

… the political conundrums involved, particularly the problem of how the richer areas … can be made to subsidize the poorer.

—Douglass Cater

2

: a riddle whose answer is or involves a pun (as in "Why didn't the lost hikers starve in the desert? Because of the sand which is there.")

Did you know?

We can only conjecture the exact origin of conundrum. What is known is that the word has been in use since the 1600s, and that it had various spellings, such as conimbrum, quonundrum, conuncrum, and quadundrum, before the current spelling was finally established in the following century. One theory of origin suggests that the word was coined as a parody of Latin by students at Oxford University, where it appears to have enjoyed particular popularity in its "word play" or "pun" sense. While the prevalent sense in this century is that of the seemingly unanswerable question or problem, frequently applied to heady dilemmas involving ethics, sociology, or economics, the word is sometimes so loosely applied to anything enigmatic as to be synonymous with puzzle or mystery.

Synonyms

• mystery
• enigma

Examples of conundrum in a Sentence

… giving parents a wealth of educational options sometimes presents a familiar inner-city conundrum: What if all your choices are bad ones? —Katherine Boo, New Yorker, 9 Apr. 2001

Mention of poor eyes and good eyes brings me to the creationist's favorite conundrum. What is the use of half an eye? —Richard Dawkins, River Out of Eden, 1995

The explanation of this conundrum is to be heard, at this very moment, on certain surreptitious radio waves, on which the voice of the American convert Bilal is … transmuted into the thunderous speech of the Imam himself. —Salman Rushdie, Harper's, December 1988

the conundrum of how an ancient people were able to build such massive structures without the benefit of today's knowledge and technology

Recent Examples on the Web

Some Halloween attractions have an ethical conundrum. —Nicole Fallert, USA Today, 27 Oct. 2025

Your gardening conundrums and successes are always welcome. —Joshua Siskin, Oc Register, 25 Oct. 2025

And when wielded skillfully, the very tools that mislead us can help us out of this conundrum. —Nadav Ziv, Time, 23 Oct. 2025

This year’s shortlist recognizes five thrilling authors, whose books all navigate uniquely American conundrums. —Brittany Allen, Literary Hub, 23 Oct. 2025

Word History

Etymology

origin unknown

First Known Use

1645, in the meaning defined at sense 2

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Kids Definition

conundrum

noun

co·​nun·​drum kə-ˈnən-drəm 

: riddle entry 1 sense 1, puzzle