Enigmatic has always meant “ambiguous, obscure, perplexing” since the adjective entered English in the 17th century. This word comes from the Latin adjective aenigmaticus, from the Greek adjective ainigmatikós, a derivative of the Greek noun aínigma (stem ainigmat- ) “a dark saying, riddle, taunt.”
Aínigma (the direct source of English enigma , meaning “a riddle or puzzling situation”) is a derivative of the verb ainíssesthai “to speak in words full of content,” then “to speak in words difficult to understand,” and finally “to speak in riddles,” a progression in meaning that seems very apt in modern life. Ainíssesthai is a derivative of the noun aînos, “tale, story” in Homer, then “meaningful words, praise, tale with a moral, fable, riddle.” This little family of Greek words, like 60 percent of Greek vocabulary, has no known etymology.

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