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conundrum

American  
[kuh-nuhn-druhm] / kəˈnʌn drəm /

noun

  1. a riddle, the answer to which involves a pun or play on words, as What is black and white and read all over? A newspaper.

  2. anything that puzzles.


conundrum British  
/ kəˈnʌndrəm /

noun

  1. a riddle, esp one whose answer makes a play on words

  2. a puzzling question or problem

"Collins English Dictionary — Complete & Unabridged" 2012 Digital Edition © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009, 2012

Etymology

Origin of conundrum

First recorded in 1590–1600; pseudo-Latin word of obscure origin

Explanation

The tricky word conundrum is used to describe a riddle or puzzle, sometimes including a play on words or pun. One of the most famous conundrums is the riddle of the Sphinx, famously in the play Oedipus the King by Sophocles. Oedipus encounters the Sphinx, a mythical beast, who asks him, "What walks on four legs in the morning, two in the afternoon, and three in the evening?" The answer is "A person": crawling as a child, walking as an adult, and using a cane in old age. The scary thing is that if the Sphinx asked you the riddle and you didn't know, she'd eat you!

Keep Reading on Vocabulary.com

Vocabulary lists containing conundrum

Example Sentences

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

Perhaps the biggest conundrum the head coach has been left with after this camp is up front.

From BBC • Apr. 1, 2026

"Until recently, while stellar rotation was thought to be part of solving this conundrum, limited computing abilities prevented us from quantitatively testing the hypothesis," says Falk Herwig, principal investigator and director of ARC.

From Science Daily • Mar. 24, 2026

The subject line of your email, to play therapist for a moment, was illuminating and revealed the heart of your conundrum.

From MarketWatch • Mar. 10, 2026

“It’s probably the number-one question, issue or conundrum we’re dealing with today,” said Aon’s global chief investment officer, Russ Ivinjack, who advises and manages money for pension plans, endowments and foundations.

From The Wall Street Journal • Mar. 2, 2026

Vivid to me, and a seeming conundrum, was the refusal of my inmate to submit to a strip-frisk.

From "Newjack: Guarding Sing Sing" by Ted Conover