Entry 2 senses · 2 variants Webster, 1913 Quandary /kwän'-dẽr-ē/ · Quan·da·ry · IPA /ˈkwɑn.də.ɹi/ n. v. t. 01 n. A state of difficulty or perplexity; doubt; uncertainty. pl. Quandaries ((#)) 1. A state of difficulty or perplexity; doubt; uncertainty. 02 v. t. To bring into a state of uncertainty, perplexity, or difficulty. 1. To bring into a state of uncertainty, perplexity, or difficulty.[Obs.]