Etymology
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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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silly (adj.)

Old English gesælig "happy, fortuitous, prosperous" (related to sæl "happiness"), from Proto-Germanic *sæligas (source also of Old Norse sæll "happy," Old Saxon salig, Middle Dutch salich, Old High German salig, German selig "blessed, happy, blissful," Gothic sels "good, kindhearted").

This is one of the few instances in which an original long e (ee) has become shortened to i. The same change occurs in breeches, and in the American pronunciation of been, with no change in spelling. [Century Dictionary]

The word's considerable sense development moved from "happy" to "blessed" to "pious," to "innocent" (c. 1200), to "harmless," to "pitiable" (late 13c.), "weak" (c. 1300), to "feeble in mind, lacking in reason, foolish" (1570s). Further tendency toward "stunned, dazed as by a blow" (1886) in knocked silly, etc. Silly season in journalism slang is from 1861 (August and September, when newspapers compensate for a lack of hard news by filling up with trivial stories). Silly Putty trademark claims use from July 1949.

It is a widespread phenomenon that the words for 'innocent', apart from their legal use, develop, through 'harmless, guileless', a disparaging sense 'credulous, naive, simple, foolish.' [Buck]
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cover (v.)
Origin and meaning of cover

mid-12c., "protect or defend from harm," from Old French covrir "to cover, protect, conceal, dissemble" (12c., Modern French couvrir), from Late Latin coperire, from Latin cooperire "to cover over, overwhelm, bury," from assimilated form of com-, here perhaps an intensive prefix (see com-), + operire "to close, cover," from PIE compound *op-wer-yo-, from *op- "over" (see epi-) + root *wer- (4) "to cover."

Sense of "to hide or screen" is from c. 1300, that of "to put something over (something else)" is from early 14c. Sense of "spread (something) over the entire extent of a surface" is from late 14c. Military sense of "aim at" is from 1680s; newspaper sense first recorded 1893; use in U.S. football dates from 1907. Betting sense "place a coin of equal value on another" is by 1857. Of a horse or other large male animal, as a euphemism for "copulate with" it dates from 1530s.

Meaning "to include, embrace, comprehend" is by 1868. Meaning "to pass or travel over, move through" is from 1818. Sense of "be equal to, be of the same extent or amount, compensate for" is by 1828. Sense of "take charge of in place of an absent colleague" is attested by 1970.

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Yankee (n.)

1683, a name applied disparagingly by Dutch settlers in New Amsterdam (New York) to English colonists in neighboring Connecticut. It may be from Dutch Janke, literally "Little John," diminutive of common personal name Jan; or it may be from Jan Kes familiar form of "John Cornelius," or perhaps an alteration of Jan Kees, dialectal variant of Jan Kaas, literally "John Cheese," the generic nickname the Flemings used for Dutchmen.

[I]t is to be noted that it is common to name a droll fellow, regarded as typical of his country, after some favorite article of food, as E[nglish] Jack-pudding, G[erman] Hanswurst ("Jack Sausage"), F[rench] Jean Farine ("Jack Flour"). [Century Dictionary, 1902, entry for "macaroni"]

Originally it seems to have been applied insultingly to the Dutch, especially freebooters, before they turned around and slapped it on the English. A less-likely theory (attested by 1832) is that it represents some southern New England Algonquian language mangling of English. In English a term of contempt (1750s) before its use as a general term for "native of New England" (1765); during the American Revolution it became a disparaging British word for all American natives or inhabitants. Contrasted with southerner by 1828. Shortened form Yank in reference to "an American" first recorded 1778. Latin-American form Yanqui attested in English by 1914 (in Mexican Spanish by 1835).

The rule observed in this country is, that the man who receives that name [Yankee] must come from some part north of him who gives it. To compensate us for giving each other nicknames, John Bull "lumps us all together," and calls us all Yankees. ["Who is a Yankee?" Massachusetts Spy, June 6, 1827]
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