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conundrum

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 February 14, 2012
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Orgy/Vomit Conundrum

The Orgy/Vomit Conundrum, coined in 1963, is the predicament in which one finds that the point of inebriation where it is possible to overcome the social barriers and anxieties in order to suggest that people in a given space engage in an orgy is also the physiological state or tipping point at which vomiting is likely to occur. In essence, you can only suggest that an orgy is in order when you are so drunk that you're bound to vomit and ruin any reasonable chance of carrying out said orgy.
by teeveeglare May 19, 2008
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Conundrum

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
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Conundrum from behind

My boyfriend caused a real conundrum from behind last night!
by Nipples14 June 16, 2016
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Toilet Paper Conundrum

The law of total probability that decides it will be your turn to be without toilet paper in the bathroom.

All at the same time, there is not a spare roll within a 12-mile radius of your location. This may have you questioning what you did to deserve this or why bad things happen to good people.
"I prayed to God asking not to be hit with the Toilet Paper Conundrum."

"I still haven't recovered from that Toilet Paper Conundrum yesterday."
by homb July 4, 2014
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Cathundrum

An unwanted situation. A shortened version for terms such as "In a pickle" or "stuck between a rock and a hard place".
Hiding from the cops in a garbage bin*

Mumbles to self; "I seem to be in a bit of a cathundrum here..."
by RedCrystalStorm June 3, 2017
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The Ross Gellar Conundrum

When an unsuspecting victim in a group of friends falls in to the bottomless pit of everyone calling them "Ross Gellar" for the rest of their life.
"I guess all my friends call me 'Ross Gellar' now. I don't really like it, but in their defense I never did try to make them stop."

"I am SO not Ross Gellar. How did you even come up with that? It doesn't make any sense and is, like, quite frankly so far off it's sad..."
"That's so Ross, bro."
"Oh my god, can't you see you are only saying that because of the Ross Gellar Conundrum?!"
by Dr. Walter Fanchy March 7, 2018
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