Etymology
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contrary (adj.)

mid-14c., "opposite, opposed, at the opposite point or in the opposite direction; extremely unlike, most unlike," from Anglo-French contrarie, Old French contrarie, and directly from Latin contrarius "opposite, opposed; contrary, reverse," from contra "against" (see contra). Meaning "given to contradiction, perverse, intractable" is from late 14c.; sense of "adverse, unfavorable" is from late 14c. Related: Contrarily.

As a noun from late 13c., "one of a pair of characters, propositions, terms, etc., the most different possible within the same class." The phrase on the contrary "in precise or extreme opposition to what has been said" is attested from c. 1400 as in the contrary.

If we take the statement All men are mortal, its contrary is Not all men are mortal, its converse is All mortal beings are men, & its opposite is No men are mortal. The contrary, however, does not exclude the opposite, but includes it as its most extreme form. Thus This is white has only one opposite, This is black, but many contraries, as This is not white, This is coloured, This is dirty, This is black; & whether the last form is called the contrary, or more emphatically the opposite, is usually indifferent. But to apply the opposite to a mere contrary (e.g. to I did not hit him in relation to I hit him, which has no opposite), or to the converse (e.g. to He hit me in relation to I hit him, to which it is neither contrary nor opposite), is a looseness that may easily result in misunderstanding; the temptation to go wrong is intelligible when it is remembered that with certain types of sentence (A exceeds B) the converse & the opposite are identical (B exceeds A). [Fowler]
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pretty (adj.)

Middle English pratie "cunning, crafty, clever" (c. 1300 as a surname), from Old English prættig (West Saxon), pretti (Kentish), *prettig (Mercian) "cunning, skillful, artful, wily, astute," from prætt, *prett "a trick, wile, craft," from Proto-Germanic *pratt- (source also of Old Norse prettr "a trick," prettugr "tricky;" Frisian pret, Middle Dutch perte, Dutch pret "trick, joke," Dutch prettig "sportive, funny," Flemish pertig "brisk, clever"), a word of unknown origin.

The connection between the Old English and Middle English words "has several points of obscurity" [OED], and except in surnames there is no record of it 13c.-14c., but they generally are considered the same. The meaning had expanded by c. 1400 to "manly, gallant," also "ingeniously or cleverly made," to "fine, pleasing to the aesthetic sense," to "beautiful in a slight way" (mid-15c.). Also used of bees (c. 1400). For sense evolution, compare nice, silly, neat (adj.), fair (adj.).

Pretty applies to that which has symmetry and delicacy, a diminutive beauty, without the higher qualities of gracefulness, dignity, feeling, purpose, etc. A thing not small of its kind may be called pretty if it is of little dignity or consequence: as a pretty dress or shade of color; but pretty is not used of men or their belongings, except in contempt. [Century Dictionary, 1897]

Of things, "fine, pleasing" 1560s. Ironical use is from 1530s (compare ironical use of fine (adj.)). The meaning "not a few, considerable, moderately large in quantity, number, extent, or duration" is from late 15c. Pretty please as an emphatic plea is attested from 1902. A pretty penny "lot of money" is recorded from 1703.

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chestnut (n.)

type of tall tree native to western Asia, southern Europe, and eastern U.S., also the large "nut" that it produces, 1560s, from chesten nut (1510s), with superfluous nut (n.) + Middle English chasteine, from Old French chastain (12c., Modern French châtaigne), from Latin castanea "chestnut, chestnut tree," from Greek kastaneia, which the Greeks explained as either "nut from Castanea" in Pontus, or "nut from Castana" in Thessaly, but probably both places are named for the trees, not the other way around, and the word is borrowed from a language of Asia Minor (compare Armenian kask "chestnut," kaskeni "chestnut tree"). In reference to the dark reddish-brown color, 1650s. Applied to the horse-chestnut by 1832.

The slang sense of "venerable joke or story" is from 1885, explained by U.S. actor Joseph Jefferson ("Lippincott's Monthly Magazine," January 1888) as probably abstracted from the 1816 melodrama "The Broken Sword" by William Dimond where an oft-repeated story involving a chestnut tree figures in an exchange between the characters "Captain Zavior" and "Pablo":

Zav. Let me see—aye! it is exactly six years since, that peace being restored to Spain, and my ship paid off, my kind brother offer'd me a snug hammock in the dwelling of my forefathers;—I mounted a mule at Barcelona, and trotted away for my native mountains. At the dawn of the fourth day's journey, I entered the wood of Collares, when, suddenly from the thick boughs of a cork-tree—
Pab. [Jumping up.] A chesnut, Captain, a chesnut!
Zav. Bah! you booby, I say, a cork.
Pab. And I swear, a chesnut—Captain! this is the twenty-seventh time I have heard you relate this story, and you invariably said, a chesnut, till now.
Zav. Did I? Well, a chesnut be it then. But, take your seat again.

Jefferson traced the connection through William Warren (1812-1888), "the veteran comedian of Boston" (and Jefferson's cousin) who often played Pablo in the melodrama.

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quiz (n.)

"brief examination by a teacher of a student or class on some subject," originally oral, 1852, colloquial, of uncertain origin.

Perhaps from quiz (v.), which might be from Latin. Or from slang quiz "odd person, person or thing deemed ridiculous" (1782, itself perhaps originally university slang), via the notion of "schoolboy prank or joke at the expense of a person deemed a quiz," a noun sense attested frequently 1840s, but quiz (n.) in the sense of "puzzling question, one designed to make one ridiculous" seems to not be attested before 1807. More than one etymological thread might be involved here. The word itself seems to have confused literary English from the beginning.

A Quiz, in the common acceptation of the word, signifies one who thinks, speaks, or acts differently from the rest of the world in general. But, as manners and opinions are as various as mankind, it will be difficult to say who shall be termed a Quiz, and who shall not: each person indiscriminately applying the name of Quiz to every one who differs from himself .... [The London Magazine, November 1783]
The word Quiz is a sort of a kind of a word
That people apply to some being absurd;
One who seems, as t'were oddly your fancy to strike
In a sort of a fashion you somehow don't like
A mixture of odd, and of queer, and all that
Which one hates, just, you know, as some folks hate a cat;
A comical, whimsical, strange, droll — that is,
You know what I mean; 'tis — in short, — 'tis a quiz!
[from "Etymology of Quiz," Charles Dibdin, 1842]

According to OED, the anecdote that credits this word to a bet by the Dublin theater-manager Daly or Daley that he could coin a word is regarded by authorities as "doubtful" and the first record of it appears to be in 1836 (in Smart's "Walker Remodelled"; the story is omitted in the edition of 1840). The medical school quiz class is attested from 1853. "The object of the Quiz will be to take the students over the ground of the different lectures in a thorough review, by a system of close questioning, so as to make them familiar with the subject-matter of the lectures to a degree not to be obtained in any other way" [Missouri Clinical Record, 1875].

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