Etymology
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infatuation (n.)
1640s, noun of action from infatuate (q.v.), or else from French infatuation or directly from Late Latin infatuationem (nominative infatuatio), from past participle stem of Latin infatuare "make a fool of."
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nugatory (adj.)

"trifling, of no value; invalid, futile," c. 1600, from Latin nugatorius "worthless, trifling, futile," from nugator "jester, trifler, braggart," from nugatus, past participle of nugari "to trifle, jest, play the fool," from nugæ "jokes, jests, trifles," a word of unknown origin.

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schlep (n.)

"stupid person, loser," 1939, short for schlepper "person of little worth" (1934), in Yiddish, "fool, beggar, scrounger," from schlep (v.) "to carry or drag." For sense evolution, compare drag (n.) "annoying dull person."

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gawp (n.)
"fool, simpleton," 1825, perhaps from gawp (v.) "to yawn, gape" (as in astonishment), which is attested from 1680s, a dialectal survival of galp (c. 1300), which is related to yelp or gape and perhaps confused with or influenced by gawk.
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bob (v.1)
"move up and down with a short, jerking motion," late 14c., probably connected to Middle English bobben "to strike in cruel jest, beat; fool, make a fool of, cheat, deceive" (early 14c.), which is perhaps from Old French bober "mock, deride," perhaps ultimately of echoic origin. Related: Bobbed; bobbing. The sense "snatch with the mouth something hanging or floating," as in bobbing for apples (or cherries), is recorded by 1799. To bob and weave in boxing is by 1928. Compare bob (n.2).
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smash (n.)

1725, "hard blow," from smash (v.). Meaning "broken-up condition" is from 1798; that of "failure, financial collapse" is from 1839. Tennis sense is from 1882. Meaning "great success" is from 1923 (Variety magazine headline, Oct. 16, in reference to Broadway productions of "The Fool" and "The Rise of Rosie O'Reilly").

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vamp (n.2)

"seductive woman who exploits men," 1911, short for vampire. First attested use is earlier than the release of the Fox film "A Fool There Was" (January 1915), with sultry Theda Bara in the role of The Vampire. The movie was based on a play of that name that had been on Broadway in 1909 (title and concept from a Kipling poem, "The Vampire," inspired by a Burne-Jones painting). The stage lead seems to have been played by Kathryn Kaelred and Bernice Golden Henderson. At any rate, Bara (born Theodosia Goodman) remains the classic vamp and the word's wide currency is attributable to her performance.

A fool there was and he made his prayer
(Even as you and I!)
To a rag and a bone and a hank of hair
(We called her the woman who did not care)
But the fool, he called her his lady fair
(Even as you and I.)
[Kipling, from "The Vampire"]
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coax (v.)

1660s, "lure with flattery and fondling," also in early use "treat endearingly" (1580s); "make a fool of, impose upon" (1670s), probably derived from slang phrases such as make a coax of, from noun coax, cox, cokes "a fool, ninny, simpleton" (1560s), which is of obscure origin, perhaps related to cock (n.1) in some sense. OED speculates that the verb was in vulgar use long before it appeared in writing, thus the order of appearance of the senses is not that of the sense development. Meaning "to manage or guide carefully" is from 1841. Related: Coaxed; coaxing.

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buffoon (n.)

1540s, "type of pantomime dance;" 1580s, "professional comic fool;" 1590s in the general sense "a clown, a joker;" from French bouffon (16c.), from Italian buffone "jester," from buffa "joke, jest, pleasantry," from buffare "to puff out the cheeks," a comic gesture, of echoic origin. Also see -oon.

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naif (adj.)

"ingenuous, artless, natural," 1590s, from French naïf, literally "naive" (see naive). The masculine form of the French word, but used in English without reference to gender. As a noun, "natural, artless, naive person," first attested 1893, from French, where Old French naif also meant "native inhabitant; simpleton, natural fool."

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