Green’s Dictionary of Slang

a dilemma, a state of extreme uncertainty.

1563		Foxe Acts and Monuments in Oliphant New Eng. i, 540: The k is prefixed; the old wandrethe (turbatio) becomes quandary [F&H].
1579		A. Munday The mirrour of mutabilitie n.p.: [H]e stood in a great quandary, not know ing what were best to doo.
1584		Herodotus [trans.] History 1-2 101: In this quandary, vncertaine what to thynke of so straunge an euent, be deuised yet to go another way.
1590		Greene Neuer Too Late in Grosart Works (1881–3) 84: Thus in a quandarie, he sate.
1609		[T]vvo notorious pyrates n.p.: This strooke Fisher into a deepe quandary, yet he knew not how to mend himselfe.
1615		A. Nixon The scourge of corruption 4: [This] put my memory into such a quandary, that I haue almost lost it.
1622		J. Taylor The great O Toole n.p.: These forc'd Rimes, fully stuft with fruitlesse labour, / Hath Curried my poore braine-pan like a Tabor: / And to recure me from this strange quandary, / Hence Vsquebaugh, and welcome sweet Canary.
1632		H. Grotius [trans.] True religion explained 319: [T]hey were driven into a quandary, often doubting what to thinke.
1641		J. Taylor Last Voyage n.p.: At my being at Hereford I vvas in a quandary or brovvne studdy.
1655		R.H. The fatall doom 81: So that [...] it were strange, if any man should now hum and haw, and be at a Quandary with himself.
1664		A. Brome Songs 151: But now they zed’s a new quandary, / Tween Pendents and Presbytary.
1670		J. Ray Proverbs 190: To be in a Quandary.
1748		Smollett Roderick Random (1979) 330: She wondered that any man [...] could, for the sake of a paultry coin, throw persons of honour into such quandries as might endanger their lives.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue n.p.: Quandary To be in a quandary: to be puzzled. Also one so over-gorged, as to be doubtful which he should do first, sh—e or spew. Some derive the term quandary from the French phrase qu’en dirai je? what shall I say of it? others from an Italian word signifying a conjuror’s circle.