“If the English language made any sense, lackadaisical would have something to do with a shortage of flowers.”
“Alack a day” or “alack the day” had its first written occurrence in Shakespeare’s Romeo and Juliet, in the cry of a heartbroken Romeo who mistakenly believes Juliet has died:
Shee’s dead, deceast, shee’s dead: alacke the day!
A couple of centuries later, the expression “ups-a-daisy” was very much in use, which is thought to be the reason why “lack-a-day” – which had by then lost its first “a” – was ornamented with a “y”, being pronounced “lack-a-daisy”.
A creative mind turned it into an adjective, – “lack-adaysical” – which was the case of the novelist Laurence Sterne.
Yet another transformation would make it into the word we say today: it lost its hyphens. The result is a single word, influenced by very different phases of the English language, its meaning travelling far from a star-crossed lover’s cry to an accusation of laziness.
Alack, also alack-a-day
Exclamation, archaic – an expression of regret or dismay
- Origin: late Middle English: probably from AH + LACK.
Exclamation, archaic – an expression of surprise, regret, or grief.
- Origin: late 17th: shortening of alack-a-day.
Adjective – lacking enthusiasm and determination; carelessly lazy […].
- Derivatives: lackadaisically, adverb
- Origin: mid 18th century (also in the sense “feebly sentimental”): from the archaic interjection lackaday,lackadaisy
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The New Oxford Dictionary of English
Gary Martin in The Phrase Finder