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pain (v.)

c. 1300, peinen, "to exert or strain oneself, strive; endeavor," from Old French pener (v.) "to hurt, cause pain," from peine, and from Middle English peine (n.); see pain (n.). Transitive meaning "cause pain; inflict pain" is from late 14c. That of "to cause sorrow, grief, or unhappiness" also is from late 14c. In Middle English also "to punish for an offense or fault; to torture, to torment." Related: Pained; paining.

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pain (n.)

late 13c., peine, "the agony suffered by Christ;" c. 1300, "punishment," especially for a crime, "legal punishment of any sort" (including fines and monetary penalties); also "condition one feels when hurt, opposite of pleasure," including mental or emotional suffering, grief, distress; from Old French peine "difficulty, woe, suffering, punishment, Hell's torments" (11c.), from Latin poena "punishment, penalty, retribution, indemnification" (in Late Latin also "torment, hardship, suffering"), from Greek poinē "retribution, penalty, quit-money for spilled blood," from PIE *kwei- "to pay, atone, compensate" (see penal).

The early "punishment" sense in English survives in phrase on pain of death. Also c. 1300 the word was used for the torments of eternal damnation after death. The sense of "exertion, effort" is from late 14c.; pains "great care taken (for some purpose), exertion or trouble taken in doing something" is recorded from 1520s.

 Phrase give (someone) a pain "be annoying and irritating" is by 1895; as a noun, localized as pain in the neck (1924) and pain in the ass (1934), though this last might have gone long unrecorded and be the original sense and the others euphemisms. First record of pain-killer "drug or herb that reduces pain" is by 1845.

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ass (n.1)

solid ungulate quadruped beast of burden of the horse kind, but smaller and with long ears and a short mane, native to southwest Asia, Old English assa (Old Northumbrian assal, assald) "he-ass." The English word is cognate with Old Saxon esil, Dutch ezel, Old High German esil, German Esel, Gothic asilus, and, beyond Germanic, Lithuanian asilas, Old Church Slavonic osl, Russian oselŭ, etc. All probably are ultimately from Latin asinus. De Vaan says the form of asinus suggests it was a loan-word into Latin, and adds, "Most IE words for 'ass' are loanwords."

Together with Greek onos it is conjectured to be from a language of Asia Minor (compare Sumerian ansu). The initial vowel of the English word might be by influence of Celtic forms (Irish and Gaelic asal), from Old Celtic *as(s)in "donkey." In Romanic tongues the Latin word has become Italian asino, Spanish asno, Old French asne, French âne.

In familiar use, the name ass is now to a great extent superseded by donkey (in Scotland cuddie); but ass is always used in the language of Scripture, Natural History, proverb, and fable; also, in ordinary use, in Ireland. [OED]

Sure-footed and patient in domestication, since ancient Greek times, in fables and parables, the animal has typified clumsiness and stupidity (hence ass-head, late 15c., etc.). To make an ass of oneself is from "A Midsummer Night's Dream" (1590). Asses' Bridge (c. 1780), from Latin Pons Asinorum, is fifth proposition of first book of Euclid's "Elements." In Middle English, someone uncomprehending or unappreciative would be lik an asse that listeth on a harpe. In 15c., an ass man was a donkey-driver.

For al schal deie and al schal passe, Als wel a Leoun as an asse. [John Gower, "Confessio Amantis," 1393]
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ass (n.2)

slang for "backside," first attested 1860 in nautical slang, in popular use from 1930; chiefly U.S.; from dialectal variant pronunciation of arse (q.v.). The loss of -r- before -s- is attested in other words (burst/bust, curse/cuss, horse/hoss, barse/bass, garsh/gash, parcel/passel).

Indirect evidence of the change from arse to ass can be traced to 17c. By 1680s arse was being pronounced to rhyme with "-ass" words, as in "Sodom or the Quintessence of Debauchery": "I would advise you, sir, to make a pass/Once more at Pockenello's loyal arse." It is perhaps as early as Shakespeare's day, if Nick Bottom transformed into a donkey in "A Midsummer Night's Dream" (1594) is the word-play some think it is.

I must to the barber's, mounsieur; for me thinks I am marvellous hairy about the face; and I am such a tender ass, if my hair do but tickle me, I must scratch. [Bottom]

By 1785 polite speakers were avoiding ass in the "donkey" sense. 

Meaning "woman regarded as a sexual object" is by early 1940s (piece of ass seems to be implied in 1930s Tijuana Bibles), but the image is older (compare buttock "a common strumpet," 1670s). To have (one's) head up (one's) ass "not know what one is doing" is attested by 1969. Colloquial (one's) ass "one's self, one's person" attested by 1958. To work (one's) ass off "work very much" is by 1946; to laugh (one's) ass off "laugh very much" is by 1972 (implied from 1965). The (stick it) up your ass oath is attested by 1953; apparent euphemisms suggest earlier use:

He snoighed up his nose as if th' cheese stunk, eyed me wi an air o contempt fro my shoon to my yed, un deawn ogen fro my yed to my shoon ; un then pushin th' brade un cheese into my hont ogen, he says "Take your vile bread and cheese and stick it up your coat sleeve, and be demmed to you. Do you think I want your paltry grub?" Un then, turnin on his heel, he hurried into th' perk. ["Bobby Shuttle un His Woife Sayroh's Visit to Manchester," 1857] 
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in (adj.)
"that is within, internal," 1590s, from in (adv.). Sense of "holding power" (the in party) first recorded c. 1600; that of "exclusive" (the in-crowd, an in-joke) is from 1907 (in-group); that of "stylish, fashionable" (the in thing) is from 1960.
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-in (1)
the adverb in attached to a verb as a word-forming element, by 1960, abstracted from sit-in, which is attested from 1941 in reference to protests and 1937 in reference to labor union actions (which probably was influenced by sit-down strike) but was popularized in reference to civil disobedience protests aimed at segregated lunch counters. As a word-forming element at first of other types of protests, extended by 1965 to any sort of communal gathering (such as love-in, 1967).
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-in (2)
word-forming element in chemistry, usually indicating a neutral substance, antibiotic, vitamin, or hormone; a modification and specialized use of -ine (2).
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in- (1)
word-forming element meaning "not, opposite of, without" (also im-, il-, ir- by assimilation of -n- with following consonant, a tendency which began in later Latin), from Latin in- "not," cognate with Greek an-, Old English un-, all from PIE root *ne- "not."

In Old French and Middle English often en-, but most of these forms have not survived in Modern English, and the few that do (enemy, for instance) no longer are felt as negative. The rule of thumb in English has been to use in- with obviously Latin elements, un- with native or nativized ones.
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smart-ass 
also smartass, 1960 (adj.), 1962 (n.), from smart (adj.) + ass (n.2).
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in (adv., prep.)

a Middle English merger of Old English in (prep.) "in, into, upon, on, at, among; about, during;" and Old English inne (adv.) "within, inside," from Proto-Germanic *in (source also of Old Frisian, Dutch, German, Gothic in, Old Norse i), from PIE root *en "in." The simpler form took on both senses in Middle English.

Sense distinction between in and on is from later Middle English, and nuances in use of in and at still distinguish British and American English (in school/at school). Sometimes in Middle English shortened to i.

The noun sense of "influence, access (to power or authorities)," as in have an in with, is first recorded 1929 in American English. to be in for it "certain to meet with something unpleasant" is from 1690s. To be in with "on friendly terms with" is from 1670s. Ins and outs "intricacies, complications of an action or course" is from 1660s. In-and-out (n.) "copulation" is attested from 1610s.

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