Origin: Pseudo-latin, used in learned social circles in Oxford University as humor, slang for "wit" or "pun" jokes, first known use 1596. Basically, answering a question with a pun, riddle, or joke. More modern usage generally refers to a difficult or complex riddle.
(In biology lab) Jim: "Hey John, I was disecting this robin, and I seem to have misplaced it's head. Have you seen it?"
John: "There you go, with your bird-brained schemes, methinks you have lost your mind!"
Jim: "Would you stop your silly conundrums and beak-flapping and help me find my dearest robin!"
by BigBadDuff October 19, 2007
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Noun:
A situation or happening that insists upon itself creating an irrational answer.
1. The phrase "Not planning ahead is planning for failure" is a conundrum. By not planning you are planning which means you aren't not planning, therefore you can't plan for failure at all, because the only way to plan for failure is to not plan at all but by not planning you are planning.
by KG Be Bosshogg. March 5, 2010
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A mysterious chemical that provides a high unlike any other. Conundrum is most commonly ingested in its liquid form, but can also be smoked, snorted, huffed, applied topically, or injected. Usually made with coke and rum and/or drank from an official "Conundrum" bottle.
"I was so high on conundrum last night that I hooked up with some random asian chick...i think"

"This is quite the conundrum"
by Point 5 September 24, 2008
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The act of envoking physical damage, most likely with a gun of some sort.
"Yo, we gotta connundrum those fools."
"Fo' real yo."
by Rasputin March 30, 2005
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In film, books, and television, when the day can conveniently be saved by a very specific skill possessed by the protagonist.

See any Aquaman story where the world is saved by talking to fish.

Coined by Marc of Angry Puppy.
The film 10,000 BC had a bad case of the Aquaman Conundrum.
by V. Ampersand July 27, 2008
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When you have the means to do something but still can’t do it. A dodo bird has wings but could not fly. Some would also describe this as not understanding why you can’t achieve a particular goal.
Giuseppe: I have done all the homework and been listening in class and gone to tutoring but i still can’t seem to pass the class
Amy: Wow it sounds like you’re facing the dodo’s conundrum
by brosifer November 15, 2019
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You think it will be fun to play the game Escape From Tarkov, however, once you play it you realize it does not meet the fun expectation you had set for it.
"Man, I want to play fun Tarkov but I do not want to run into The Tarkov Conundrum."
by DrCamel May 30, 2021
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