Etymology
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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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pipsqueak (n.)

also pip-squeak, contemptuous name for an insignificant person, 1910, from the trivial noise a young or weak creature makes. In World War I it was the soldier's slang name for a small German shell "which makes both a pip and a squeak when it comes over the trenches" [Farrow, "Dictionary of Military Terms," 1918]. Pip and Squeak (and later Wilfred), the beloved English comic strip animals, debuted May 1919 in the children's section of the Daily Mirror. To squeeze (something) until the pips squeak "exact the maximum from" is attested by 1918, from pip (n.1).  

The grossest spectacle was provided by Sir Eric Geddes in the Guildhall at Cambridge. An earlier speech in which, in a moment of injudicious candour, he had cast doubts on the possibility of extracting from Germany the whole cost of the war had been the object of serious suspicion, and he had therefore a reputation to regain. "We will get out of her all you can squeeze out of a lemon and a bit more," the penitent shouted, "I will squeeze her until you can hear the pips squeak" ; his policy was to take every bit of property belonging to Germans in neutral and Allied countries, and all her gold and silver and her jewels, and the contents of her picture-galleries and libraries, to sell the proceeds for the Allies' benefit. [John Maynard Keynes, "The Economic Consequences of Peace," 1919]
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pocket (adj.)

1610s, "of or pertaining to or meant for a pocket," from pocket (n.). Pocket-money "money for occasional or trivial purposes" is attested from 1630s; pocket-handkerchief is from 1640s. Often merely implying a small-sized version of something (for example of of warships, from 1930; also compare Pocket Venus "beautiful, small woman," attested from 1808). Pocket veto attested from 1842, American English.

The "pocket veto" can operate only in the case of bills sent to the President within ten days of Congressional adjournment. If he retain such a bill (figuratively, in his pocket) neither giving it his sanction by signing it, nor withholding his sanction in returning it to Congress, the bill is defeated. The President is not bound to give reasons for defeating a bill by a pocket veto which he has not had at least ten days to consider. In a regular veto he is bound to give such reasons. [James Albert Woodburn, "The American Republic and its Government," Putnam's, 1903]

In English history a pocket borough (by 1798) was one whose parliamentary representation was under the control of one person or family.

BRAMBER, Sussex. This is one of the burgage-tenure or nomination boroughs. The place altogether consists only of twenty-two miserable thatched cottages, and is composed of two intersections of a street, the upper and middle parts of which constitute another pocket borough, called Steyning, which we shall notice in the second class, as belonging to the Duke of Norfolk. ["A Key to the House of Commons," London, 1820]
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small (adj.)

Old English smæl "thin, slender, narrow; fine," from Proto-Germanic *smal- "small animal; small" (source also of Old Saxon, Danish, Swedish, Middle Dutch, Dutch, Old High German smal, Old Frisian smel, German schmal "narrow, slender," Gothic smalista "smallest," Old Norse smali "small cattle, sheep"), perhaps from a PIE root *(s)melo- "smaller animal" (source also of Greek melon, Old Irish mil "a small animal;" Old Church Slavonic malu "bad"). Original sense of "narrow" now almost obsolete, except in reference to waistline and intestines.

My sister ... is as white as a lilly, and as small as a wand. [Shakespeare, "Two Gentlemen of Verona," 1591]

Sense of "not large, of little size" developed in Old English. Of children, "young," from mid-13c. Meaning "inferior in degree or amount" is from late 13c. Meaning "trivial, unimportant" is from mid-14c. Sense of "having little property or trade" is from 1746. That of "characterized by littleness of mind or spirit, base, low, mean" is from 1824. As an adverb by late 14c.

Small fry, first recorded 1690s of little fish, 1885 of insignificant people. Small potatoes "no great matter, something petty or insignificant" is attested by 1924; small change "something of little value" is from 1902; small talk "chit-chat, trifling conversation" (1751) first recorded in Chesterfield's "Letters." Small world as a comment upon an unexpected meeting of acquaintances is recorded from 1895. Small-arms, indicating those capable of being carried in the hand (contrasted to ordnance) is recorded from 1710.

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pun (n.)

"a Conceit arising from the use of two Words that agree in the Sound, but differ in the Sense" [Addison]; "An expression in which the use of a word in two different applications, or the use of two different words pronounced alike or nearly alike, presents an odd or ludicrous idea" [Century Dictionary]; 1660s (first attested in Dryden), a word of uncertain origin.

Perhaps from pundigron, meaning the same thing (though attested first a few years later), itself a word of uncertain etymology, perhaps a humorous alteration of Italian puntiglio "equivocation, trivial objection," diminutive of Latin punctum "point." This is pure speculation. Punnet was another early form.

Pun was prob. one of the clipped words, such as cit, mob, nob, snob, which came into fashionable slang at or after the Restoration. [OED]

 The verb, "to make puns," also is attested from 1660s, first in Dryden. Related: Punned; punning.

At the revival of learning, and the spread of what we may term the refinement of society, punning was one of the few accomplishments at which the fine ladies and gentlemen aimed. From the twelfth to the sixteenth century, it was at its greatest height. The conversation of the witty gallants, and ladies, and even of the clowns and other inferior characters, in the comedies of Shakespeare and his contemporaries, which we may be sure was painted from the life, is full of puns and plays upon words. The unavoidable result of such an excess was a surfeit, and the consequent dégout, which lasted for more than a century. Like other diseases, it broke out again subsequently with redoubled virulence, and made great havoc in the reign of Queen Anne. [Larwood & Hotten, "The History of Signboards from the Earliest Times to the Present Day," London, 1867] 
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