Quandary

n.	1.	A state of difficulty or perplexity; doubt; uncertainty.
v. t.	1.	To bring into a state of uncertainty, perplexity, or difficulty.

Noun	1.	quandary - a situation from which extrication is difficult especially an unpleasant or trying one; "finds himself in a most awkward predicament"; "the woeful plight of homeless people" Synonyms: plight, predicament
	2.	quandary - state of uncertainty or perplexity especially as requiring a choice between equally unfavorable options Synonyms: dilemma

Gordian knot, baffle, bafflement, bother, confoundment, crux, discomposure, disconcert, disconcertedness, disconcertion, disconcertment, disturbance, embarrassment, enigma, jam, knot, knotty point, mystery, node, nodus, nonplus, oxymoron, paradox, perturbation, pickle, pons asinorum, poser, pother, problem, puzzlement, riddle, scrape, stew, teaser, unassuredness, upset, vexed question