Etymology
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bewilder (v.)

1680s, "confuse as to direction or situation," also, figuratively, "perplex, puzzle, confuse," from be- "thoroughly" + archaic wilder "lead astray, lure into the wilds," which probably is a back-formation from wilderness. An earlier word with the same sense was bewhape (early 14c.) and there is a 17c. use of bewhatle.

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crossword (adj.)

as the name of a game in which clues suggests words that are written in overlapping horizontal and vertical boxes in a grid, January 1914, from cross (adj.) + word (n.). The first one ran in the "New York World" newspaper Dec. 21, 1913, but was called word-cross. As a noun, 1925, short for crossword puzzle.

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pose (v.2)

"to puzzle, confuse, perplex," 1590s, earlier "to put questions to, interrogate closely" (1520s), probably from French poser "suppose, assume," from Old French poser "to put, place, set" (see pose (v.1)). Also in some cases a shortening of English appose "examine closely," and directly from oppose (of which appose was a variant). Related: Posed; posing.

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nonplus (v.)

"to bring to a nonplus, to perplex, puzzle, confound," 1590s, from the noun nonplus "state in which one is unable to proceed or decide" (1580s), usually in a phrase such as at or to a nonplus, properly "state where 'nothing more' can be done or said," from Latin non plus "no more, no further" (see plus). Related: Nonplussed.

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logogram (n.)

"word-sign, sign or character representing a word," 1840, from logo- "word" + -gram. Generically, "any symbol representing graphically a product, idea, etc.," from 1966. The earliest use of the word (1820) is in the sense "logograph," but OED explains this as a substitute for logograph, "which in this sense is itself a mistake for logogriph," the old type of word-puzzle.

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floor (v.)

early 15c., "to furnish with a floor," from floor (n.). Sense of "puzzle, confound" is from 1830, a figurative use, from earlier sense of "knock down to the floor" (1640s). Colloquial floor it "press down hard on the accelerator pedal of a motor vehicle" is by 1986 (compare earlier step on it in the same sense). In mid-19c. English university slang, it meant "do thoroughly and successfully" (1852). Related: Floored; flooring.

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logogriph (n.)

type of word puzzle based on synonyms, etc., and often in the form of a verse, 1590s, from French logogriphe, from Greek logos "word" (see Logos) + gripos/griphos "riddle," a figurative use, literally "fishing basket, creel," probably from a pre-Greek word in a lost Mediterranean language. "The variation [p/ph] is typical for Pre-Greek words; such an origin for a fisherman's word is quite understandable" [Beekes].

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intrigue (v.)

1610s, "to trick, deceive, cheat," from French intriguer (16c.), from Italian intrigare "to plot, meddle; perplex, puzzle," from Latin intricare "to entangle, perplex, embarrass" (see intricate).

Meaning "to plot or scheme" is recorded by 1714. That of "to excite curiosity" is from 1894 (OED calls this use "A modern gallicism"). It also could mean "carry on a clandestine or illicit sexual relationship" (1650s). The word appears earlier in English as entriken "entangle, ensnare; involve in perplexity, embarrass" (late 14c.), from Old French entrique or directly from the Latin verb. Related: Intrigued; intriguer; intriguing. Dutch intrigueren, German intriguiren are from French.

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queer (v.)

"to spoil, ruin," 1812, slang, from queer (adj.). Related: Queered; queering. Earlier it meant "to puzzle, ridicule, deride, cheat" (1790). To queer the pitch (1846) is in reference to the patter of an itinerant tradesman or showman (see pitch (n.1)).

These wanderers, and those who are still seen occasionally in the back streets of the metropolis, are said to 'go a-pitching ;' the spot they select for their performance is their 'pitch,' and any interruption of their feats, such as an accident, or the interference of a policeman, is said to 'queer the pitch,'—in other words, to spoil it. [Thomas Frost, "Circus Life and Circus Celebrities," London, 1875]
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perplex (v.)

1590s, "embarrass, puzzle, bewilder, fill (someone) with uncertainty," evidently a back-formation from perplexed, a variant of the adjective perplex (late 14c.), "perplexed, puzzled, bewildered," from Latin perplexus "involved, confused, intricate;" but Latin had no corresponding verb *perplectere. The Latin compound would be per "through" (from PIE root *per- (1) "forward," hence "through") + plexus "entangled," past participle of plectere "to twine, braid, fold" (from suffixed form of PIE root *plek- "to plait").

The form of the English adjective began to shift to perplexed by late 15c., probably to conform to other past-participle adjectives, and the adjective perplex became obsolete from 17c. The verb is the latest attested of the group. The sense of "make intricate, involve, entangle, make difficult to be understood" is from 1610s. Related: Perplexing, which well describes the history of the word; perplexingly.

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