"A word game or joke, comprising a question or statement couched in deliberately puzzling terms, propounded for solving by the hearer/reader using clues embedded within that wording" [Oxford Dictionary of English Folklore], early 13c., redels, from Old English rædels "riddle; counsel; conjecture; imagination; discussion," common Germanic (Old Frisian riedsal "riddle," Old Saxon radisli, Middle Dutch raetsel, Dutch raadsel, Old High German radisle, German Rätsel "riddle").

The first element is from Proto-Germanic *redaz- (from PIE *re-dh-, from root *re- "to reason, count"). The ending is Old English noun suffix -els, the -s of which later was mistaken for a plural affix and stripped off in early Modern English. The meaning "anything which puzzles or perplexes" is from late 14c.

game similar to billiards, 1848, originally (1690s) the name of a card game played for collective stakes, from pool "collective stakes of players in a game," which is from French poule "stakes, booty, plunder," literally "hen," from Old French poille "hen, young fowl," from Vulgar Latin *pulla, fem. of Latin pullus "young animal," especially "young fowl," from PIE root *pau- (1) "few, little."

Perhaps the original notion is from jeu de la poule, supposedly a game in which people threw things at a chicken and the player who hit it, won it, which speaks volumes about life in the Middle Ages. The notion behind the word, then, is "playing for money." The connection of "hen" and "stakes" is also present in Spanish polla and Walloon paie.

By 1868 it came to mean "combination of a number of persons, each staking a sum of money on the success of a horse in a race, a contest in a game, etc., the money to be divided among the successful bettors," thus also "collective stakes" in betting. The sense of "common reservoir of resources" is from 1917. Meaning "group of persons who share duties or skills" (typist pool, etc.) is from 1928. From 1933 as short for football pool in wagering.

Pool shark is from 1898. The phrase dirty pool "underhanded or unsportsmanlike conduct," especially in politics (1951), seems to belong here now, but the phrase dirty pool of politics, with an image of pool (n.1) is recorded from 1871 and was in use early 20c.

"unkempt; having rough, coarse, long hair," 1580s, from shag (n.) + -y (2). Related: Shaggily; shagginess. Earlier was shagged, from Old English sceacgede "hairy;" compare Old Norse skeggjaðr, Danish skægget "bearded." The shaggy-dog story as a type of absurd joke built into a long, tedious story, is attested from 1943 and was a fad in the mid-40s. The origin of the phrase may be in vaudeville; the most-often cited original example involves an Englishman who offers a reward for a lost shaggy dog, an enterprising American who, with great difficulty, tracks him down and offers a shaggy dog that he claims is the one, and his curt reception: "Not that shaggy." But the story does not seem to be older than the phrase.

mid-14c., "demon;" late 14c., "a ragged lout," also in surnames (Isabella Ragamuffyn, 1344), from Middle English raggi "ragged" ("rag-y"?) + "fanciful ending" [OED], or else perhaps second the element is Middle Dutch muffe "mitten." Or, as Johnson has it, "From rag and I know not what else."

Ragged was used of the devil from c. 1300 in reference to his "shaggy" appearance. Raggeman (late 13c. as a surname, presumably "one who goes about in tattered clothes") was used by Langland as the name of a demon (late 14c.), and compare Old French Ragamoffyn, name of a demon in a mystery play. Sense of "dirty, disreputable boy" is from 1580s. Also compare ragabash "idle, worthless fellow" (c. 1600).

also molly-coddle, by 1839 (implied in mollycoddling), from a noun (by 1828) meaning "overly pampered, fastidious, effeminate male," from Molly (pet name formation from Mary), which had been used contemptuously at least since 1707 for "a milksop, an effeminate man" (see molly (n.1)) + coddle (q.v.). Related: Mollycoddled.

All his pursuits had been sedentary; for he never went out but with his mother. He was not allowed to stroll about the farm with his father, lest he should get his clothes dirty and his feet wet. In short, he was what Giles Darman pronounced him to be—"a little mollycoddle." ["Babbington Droneham," Hood's Magazine, March 1844]

1841, "a young cod, split and fried or boiled," a New England word of uncertain origin, possibly from Dutch schrood "piece cut off," from Middle Dutch scrode "shred" (cognate with Old English screade "piece cut off;" see shred (n.)). If this is the origin, the notion is probably of fish cut into pieces for drying or cooking.

A Boston brahmin is on a business trip to Philadelphia. In search of dinner, and hungry for that Boston favorite, broiled scrod, he hops into a cab and asks the driver, "My good man, take me someplace where I can get scrod." The cabbie replies, "Pal, that's the first time I've ever been asked that in the passive pluperfect subjunctive." [an old joke in Philadelphia, this version of it from "Vex, Hex, Smash, Smooch," Constance Hale, 2012]

1762, "one who bounces," agent noun from bounce (v.), which originally meant "to thump, hit." Given various specific senses in 19c., such as "boaster, bully, braggart" (1833); also "large example of its kind" (1842); "enforcer of order in a bar or saloon" (1865, American English, originally colloquial).

Now it so happened that the brakeman was what is known, in the language of the road, as a "bouncer." That is, he was a hybrid combining the qualities of a brakeman and a bruiser, and was frequently called into requisition by the conductor to take the dirty work of ejecting tramps off of his hands. ["Staats," "A Tight Squeeze," 1879]

"The Bouncer" is merely the English "chucker out". When liberty verges on license and gaiety on wanton delirium, the Bouncer selects the gayest of the gay, and — bounces him! [London Daily News, July 26, 1883]

1086, Cestre Scire, from Chester + scir "district" (see shire). Cheshire cat and its proverbial grin are attested from 1770, but the signification is obscure.

I made a pun the other day, and palmed it upon Holcroft, who grinned like a Cheshire cat. (Why do cats grin in Cheshire?—Because it was once a county palatine, and the cats cannot help laughing whenever they think of it, though I see no great joke in it.) I said that Holcroft, on being asked who were the best dramatic writers of the day, replied, "HOOK AND I." Mr Hook is author of several pieces, Tekeli, &c. You know what hooks and eyes are, don't you? They are what little boys do up their breeches with. [Charles Lamb, letter to Thomas Manning, Feb. 26, 1808]

used by U.S. scholar Brander Matthews in 1906 in "American Character;" popularized 1907 by U.S. humorist Frank Gelett Burgess. Originally mocking excessive praise printed on book jackets, and probably derisively imitative.

Gelett Burgess ... then entertained the guests with some characteristic flashes of Burgessian humor. Referring to the word "blurb" on the wrapper of his book he said: "To 'blurb' is to make a sound like a publisher. The blurb was invented by Frank A. Munsey when he wrote on the front of his magazine in red ink 'I consider this number of Munsey's the hottest pie that ever came out of my bakery.' ... A blurb is a check drawn on Fame, and it is seldom honored.["] [Publishers' Weekly, May 18, 1907]

Burgess occasionally wrote for Munsey's popular magazine, but the origin story in the joke shouldn't be taken seriously.

1540s, "joke, jest, stroke of wit, contemptuous remark," from flirt (v.). By 1560s as "a pert young hussey" [Johnson], and Shakespeare has flirt-gill (i.e. Jill) "a woman of light or loose behavior" (Fletcher formalizes it as flirt-gillian), while flirtgig was a 17c. Yorkshire dialect word for "a giddy, flighty girl." One of the many fl- words suggesting loose, flapping motion and connecting the notions of flightiness and licentiousness. Compare English dialect and Scottish flisk "to fly about nimbly, skip, caper" (1590s); source of Scott's fliskmahoy "girl giddy and full of herself." The meaning "person who plays at courtship" is from 1732 (as the name of female characters in plays at least since 1689 (Aphra Behn's "The Widow Ranter")). Also in early use sometimes "person one flirts with," though by 1862 this was being called a flirtee.