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1.
n. Origin unknown. 1. A kind of riddle based upon some fanciful or fantastic resemblance between things quite unlike; a puzzling question, of which the answer is or involves a pun.

Or pun ambiguous, or conundrum quaint. --J. Philips.

2. A question to which only a conjectural answer can be made.
Do you think life is long enough to let me speculate on conundrums like that? --W. Black.
by Conundrum August 12, 2002
 
2.
A difficult problem...often used in matters of the heart. The ability to appreciate what you have and want to do well by it, and the overwhelming emotion towards someone else, that feels too good to ignore.
I love my partner for all the wonderful qualities they possess and for the unconditional love and support they provide.

What is lacking however...I've found in you. What a conundrum....now what?
by Whiskeybent September 23, 2009
 
3.
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 18, 2007
 
4.
A fun word to say that describes your friends constant on and off relationship with a girl. Usually is used in replacement to the girl's name
DJ, I'm serious as much as you want me too i am not going to help out with the conundrum that is your ex.
by Brycemiller January 16, 2009
 
5.
A difficult and confusing problem or question. They'll piss you off and are often found in crossword puzzles.
Before he could even finish reading 17 across, Sean realized that the cruciverbalist otherwise known as Brandi had answered the conundrum in the white and shaded squares.
by medium sean January 23, 2012
 
6.
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 04, 2010
 
7.
1. answering someone with a pun

2. a dilema of some sort, can't be answered

also see <b>kunundrum</b>
The answer to the cure of aids is a conundrum.
by kdv June 28, 2005