quandary

[kwon-duh-ree, -dree]
noun, plural quandaries.
a state of perplexity or uncertainty, especially as to what to do; dilemma.

Origin:
1570–80; perhaps fancifully < Latin quand(ō) when + -āre infinitive suffix


See predicament.
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World English Dictionary
quandary (ˈkwɒndrɪ, -dərɪ)
 
n , pl -ries
a situation or circumstance that presents problems difficult to solve; predicament; dilemma
 
[C16: of uncertain origin; perhaps related to Latin quandō when]

Collins English Dictionary - Complete & Unabridged 10th Edition
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Etymonline
Word Origin & History

quandary
1579, "state of perplexity," of unknown origin, perhaps a quasi-Latinism based on L. quando "when."
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
These abstruse works are nevertheless worth the effort, giving a unique spin on
  the quandary of living in an inexplicable world.
He is in a quandary or quite confused.
We have long been in a quandary over a name for the boat.
Investors are in a quandary because no one knows how the stock market will
  behave this summer.
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