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
In an ideal world, the answer to such quandaries would be elections to produce
  a new leadership with a clear mandate.
Both suffer familiar urban quandaries of frustration and decay.
These quandaries are inescapable in a large democracy, especially one that is a
  global hegemon.
The moral quandaries and bioethical concerns underlying these restrictions
  can't be dismissed.
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