Etymology
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O 

fifteenth letter of the alphabet, from a character that in Phoenician was called  'ain (literally "eye") and represented "a very peculiar and to us unpronounceable guttural" [Century Dictionary]. The Greeks also lacked the sound, so when they adopted the Phoenician letters they arbitrarily changed O's value to a vowel. (Thus there is no grounds for the belief that the form of the letter represents the shape of the mouth in pronouncing it.) The Greeks later added a special character for "long" O (omega), and the original became "little o" (omicron).

In Middle English and later colloquial use, o or o' can be an abbreviation of on or of, and is still literary in some words (o'clock, Jack-o'-lantern, tam-o'-shanter, cat-o'-nine-tails, will-o'-the-wisp, etc.).

O' the common prefix in Irish surnames is from Irish ó, ua (Old Irish au, ui) "descendant." 

The "connective" -o- is the usual connecting vowel in compounds taken or formed from Greek, where it often is the vowel in the stem. "[I]t is affixed, not only to terms of Greek origin, but also to those derived from Latin (Latin compounds of which would have been formed with the L. connecting or reduced thematic vowel, -i), especially when compounds are wanted with a sense that Latin composition, even if possible, would not warrant, but which would be authorized by the principles of Greek composition." [OED]

As "zero" in Arabic numerals it is attested from c. 1600, from the similarity of shape. Similarly the O blood type (1926) was originally "zero," denoting the absence of A and B agglutinogens.

As a gauge of track in model railroads, by 1905. For o as an interjection of fear, surprise, joy, etc., see oh.

The use of the colloquial or slang -o suffix in wino, ammo, combo, kiddo, the names of the Marx Brothers, etc., "is widespread in English-speaking countries but nowhere more so than in Australia" [OED].

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thee (pron.)

Old English þe (accusative and dative singular of þu "thou"), from Proto-Germanic *theke (source also of Old Frisian thi, Middle Dutch di, Old High German dih, German dich, Old Norse þik, Norwegian deg, Gothic þuk), from PIE *tege-, accusative of root *tu-, second person singular pronoun (see thou). The verb meaning "to use the pronoun 'thee' to someone" is recorded from 1662, in connection with the rise of Quakerism.

In Middle English, people began to use plural forms in all cases, at first as a sign of respect to superiors, then as a courtesy to equals. By the 1600s, the singular forms had come to represent familiarity and lack of status, and fell from use except in the case of a few dialects, notably in the north of England. People in Lancashire north of the Rossendale Forest and Yorkshire formerly were noted for use of the singular second person pronouns tha (nom.) and thee (acc.). For religious reasons (Christian equality of persons, but also justified as grammatically correct), the Quakers also retained the familiar forms.

Thou and Thee was a sore cut to proud flesh and them that sought self-honour, who, though they would say it to God and Christ, could not endure to have it said to themselves. So that we were often beaten and abused, and sometimes in danger of our lives, for using those words to some proud men, who would say, "What! you ill-bred clown, do you Thou me?" as though Christian breeding consisted in saying You to one; which is contrary to all their grammar and teaching books, by which they instructed their youth. [George Fox's journal, 1661]
While the Quakers originally adopted "thee" and "thou" on account of their grammatical correctness, they soon fell into the careless habit of using "thee," the objective, instead of "thou," the nominative. Common illustrations are: "How does thee do?" or "Will thee," etc. [George Fox Tucker, "A Quaker Home," Boston, 1891]
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back (n.)

Old English bæc "back," from Proto-Germanic *bakam (cognates: Old Saxon and Middle Dutch bak, Old Frisian bek), with no known connections outside Germanic. In other modern Germanic languages the cognates mostly have been ousted in this sense by words akin to Modern English ridge (such as Danish ryg, German Rücken).

Many Indo-European languages show signs of once having distinguished the horizontal back of an animal (or a mountain range) from the upright back of a human. In other cases, a modern word for "back" may come from a word related to "spine" (Italian schiena, Russian spina) or "shoulder, shoulder blade" (Spanish espalda, Polish plecy).

By synecdoche, "the whole body," especially with reference to clothing. Meaning "upright part of a chair" is from 1520s. To turn (one's) back on (someone or something) "ignore" is from early 14c. As a U.S. football position by 1876, so called from being behind the line of rushers; further distinguished according to relative position as quarterback, halfback, fullback.

To know (something) like the back of one's hand, implying familiarity, is first attested 1893 in a dismissive speech made to a character in Robert Louis Stevenson's "Catriona":

If I durst speak to herself, you may be certain I would never dream of trusting it to you; because I know you like the back of my hand, and all your blustering talk is that much wind to me.

The story, a sequel to "Kidnapped," has a Scottish setting and context, and the back of my hand to you was noted in the late 19th century as a Scottish expression meaning "I will have nothing to do with you" [see Longmuir's edition of Jamieson's Scottish dictionary]. In English generally, the back of (one's) hand has been used to imply contempt and rejection at least since 1300. Perhaps the connection of a menacing dismissal is what made Stevenson choose that particular anatomical reference.

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be (v.)

Old English beon, beom, bion "be, exist, come to be, become, happen," from Proto-Germanic *biju- "I am, I will be." This "b-root" is from PIE root *bheue- "to be, exist, grow," and in addition to the words in English it yielded German present first and second person singular (bin, bist, from Old High German bim "I am," bist "thou art"), Latin perfective tenses of esse (fui "I was," etc.), Old Church Slavonic byti "be," Greek phu- "become," Old Irish bi'u "I am," Lithuanian būti "to be," Russian byt' "to be," etc.

The modern verb to be in its entirety represents the merger of two once-distinct verbs, the "b-root" represented by be and the am/was verb, which was itself a conglomerate. Roger Lass ("Old English") describes the verb as "a collection of semantically related paradigm fragments," while Weekley calls it "an accidental conglomeration from the different Old English dial[ect]s." It is the most irregular verb in Modern English and the most common. Collective in all Germanic languages, it has eight different forms in Modern English:

BE (infinitive, subjunctive, imperative); AM (present 1st person singular); ARE (present 2nd person singular and all plural); IS (present 3rd person singular); WAS (past 1st and 3rd persons singular); WERE (past 2nd person singular, all plural; subjunctive); BEING (progressive & present participle; gerund); BEEN (perfect participle).

The paradigm in Old English was: eom, beo (present 1st person singular); eart, bist (present 2nd person singular); is, bið (present 3rd person singular);  sind, sindon, beoð (present plural in all persons); wæs (past 1st and 3rd person singular); wære (past 2nd person singular); wæron (past plural in all persons); wære (singular subjunctive preterit); wæren (plural subjunctive preterit).

The "b-root" had no past tense in Old English, but often served as future tense of am/was. In 13c. it took the place of the infinitive, participle and imperative forms of am/was. Later its plural forms (we beth, ye ben, they be) became standard in Middle English and it made inroads into the singular (I be, thou beest, he beth), but forms of are claimed this turf in the 1500s and replaced be in the plural. For the origin and evolution of the am/was branches of this tangle, see am and was.

That but this blow Might be the be all, and the end all. ["Macbeth" I.vii.5]
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penny (n.)

English coin, Middle English peni, from Old English pening, penig, Northumbrian penning "penny," from Proto-Germanic *panninga- (source also of Old Norse penningr, Swedish pänning, Danish penge, Old Frisian panning, Old Saxon pending, Middle Dutch pennic, Dutch penning, Old High German pfenning, German Pfennig, not recorded in Gothic where skatts is used instead), a word of unknown origin.

Offa's reformed coinage on light, broad flans is likely to have begun c.760-5 in London, with an awareness of developments in Francia and East Anglia. ... The broad flan penny established by Offa remained the principal denomination, with only minor changes, until the fourteenth century. [Anna Gannon, "The Iconography of Early Anglo-Saxon Coinage," Oxford, 2003]

The English coin was originally set at one-twelfth of a shilling (or 240 to a Tower pound) and was of silver, later copper, then bronze. There are two plural forms: pennies of individual coins, pence collectively. In Middle English, any coin could be called a penny, and in translations it rendered various foreign coins of small denomination, especially Latin denarius, whence comes its abbreviation d.

As an American English colloquial for cent, it is recorded by 1889. In reference to nails, "a pound," denoting that 1,000 nails will weigh so much, OED says it probably is based originally on the price per 100 and persisted as prices fell.

Penny-a-liner "writer for a journal or newspaper" is attested by 1830, from their supposed rate of pay. Penny dreadful in reference to "cheap and gory fiction" dates from 1870. Phrase penny-wise and pound-foolish is recorded from c. 1600.

Penny-pincher "miserly person" is recorded from 1906 (Middle English had pinchpenny (n.) in that sense; as an adjective penny-pinching is recorded from 1858, American English). Penny loafers attested from 1960, perhaps from the fashion of slipping a penny into the slits of the bands across the facing.

"A regular penny-a-liner is a person who supplies the newspapers of the city with short articles of news, ingenious remarks upon the current topics of the day, reports of meetings, or of cases in the police offices, accidents, &c. &c., but who, observe, has no express engagement from, or any direct connexion with, any newspaper whatever. His success is wholly precarious—always uncertain. If the contributions which those persons forward for publication, in this way, are published, they are certain of payment for them at the rate of one penny, three half-pence, and in rare cases, two pence a-line, according to the importance of the subject matter supplied. ["The London Penny-a-Line System," Irish Monthly Magazine, January 1833]
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so long (interj.)

parting salutation, 1860, of unknown origin, perhaps from a German idiom (compare German parting salutation adieu so lange, the full sense of which probably is something like "farewell, whilst (we're apart)"); or perhaps from Hebrew shalom (via Yiddish sholom). Some have noted a similarity to Scandinavian leave-taking phrases, such as Norwegian Adjø så lenge, Farvel så lenge, Mor'n så lenge, literally "bye so long, farewell so long, morning so long;" and Swedish Hej så länge "good-bye for now," with så länge "for now" attested since 1850 according to Swedish sources. Most etymology sources seem to lean toward the German origin. So long (adv.) "for such a long time" is from late Old English.

Earlier guesses that it was a sailors' corruption of a South Pacific form of Arabic salaam are not now regarded as convincing. "Dictionary of American Slang" also adds to the list of candidates Irish slán "safe," said to be used as a salutation in parting. The phrase seems to have turned up simultaneously in America, Britain, and perhaps Canada, originally among lower classes. First attested use is in title and text of the last poem in Whitman's "Leaves of Grass" in the 1860 edition.

An unknown sphere, more real than I dream'd, more direct, darts awakening rays about me — So long!
Remember my words — I may again return,
I love you — I depart from materials;
I am as one disembodied, triumphant, dead.

Whitman's friend and fan William Sloane Kennedy wrote in 1923:

The salutation of parting — 'So long!' — was, I believe, until recent years, unintelligible to the majority of persons in America, especially in the interior, and to members of the middle and professional classes. I had never heard of it until I read it in Leaves of Grass, but since then have quite often heard it used by the laboring class and other classes in New England cities. Walt wrote to me, defining 'so long' thus: "A salutation of departure, greatly used among sailors, sports, & prostitutes — the sense of it is 'Till we meet again,' — conveying an inference that somehow they will doubtless so meet, sooner or later." ... It is evidently about equivalent to our 'See you later.' The phrase is reported as used by farm laborers near Banff, Scotland. In Canada it is frequently heard; 'and its use is not entirely confined to the vulgar.' It is in common use among the working classes of Liverpool and among sailors at Newcastle-upon-Tyne, and in Dorsetshire. ... The London Globe suggests that the expression is derived from the Norwegian 'Saa laenge,' a common form of 'farewell,' au revoir. If so, the phrase was picked up from the Norwegians in America, where 'So long' first was heard. The expression is now (1923) often used by the literary and artistic classes.
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gay (adj.)
Origin and meaning of gay

late 14c., "full of joy, merry; light-hearted, carefree;" also "wanton, lewd, lascivious" (late 12c. as a surname, Philippus de Gay), from Old French gai "joyful, happy; pleasant, agreeably charming; forward, pert; light-colored" (12c.; compare Old Spanish gayo, Portuguese gaio, Italian gajo, probably French loan-words). Ultimate origin disputed; perhaps from Frankish *gahi (related to Old High German wahi "pretty"), though not all etymologists accept this.

Meaning "stately and beautiful; splendid and showily dressed" is from early 14c. Of things, "sumptuous, showy, rich, ornate," mid-14c. of colors, etc., "shining, glittering, gleaming, bright, vivid," late 14c.; of persons, "dressed up, decked out in finery," late 14c.

In the English of Yorkshire and Scotland formerly it could mean "moderately, rather, considerable" (1796; compare sense development in pretty (adj.)).

The word gay by the 1890s had an overall tinge of promiscuity -- a gay house was a brothel. The suggestion of immorality in the word can be traced back at least to the 1630s, if not to Chaucer:

But in oure bed he was so fressh and gay
Whan that he wolde han my bele chose.

Slang meaning "homosexual" (adj.) begins to appear in psychological writing late 1940s, evidently picked up from gay slang and not always easily distinguished from the older sense:

After discharge A.Z. lived for some time at home. He was not happy at the farm and went to a Western city where he associated with a homosexual crowd, being "gay," and wearing female clothes and makeup. He always wished others would make advances to him. [Rorschach Research Exchange and Journal of Projective Techniques, 1947, p.240]

The association with (male) homosexuality likely got a boost from the term gay cat, used as far back as 1893 in American English for "young hobo," one who is new on the road, also one who sometimes does jobs.

"A Gay Cat," said he, "is a loafing laborer, who works maybe a week, gets his wages and vagabonds about hunting for another 'pick and shovel' job. Do you want to know where they got their monica (nickname) 'Gay Cat'? See, Kid, cats sneak about and scratch immediately after chumming with you and then get gay (fresh). That's why we call them 'Gay Cats'." [Leon Ray Livingston ("America's Most Celebrated Tramp"), "Life and Adventures of A-no. 1," 1910]

Quoting a tramp named Frenchy, who might not have known the origin. Gay cats were severely and cruelly abused by "real" tramps and bums, who considered them "an inferior order of beings who begs of and otherwise preys upon the bum -- as it were a jackal following up the king of beasts" [Prof. John J. McCook, "Tramps," in "The Public Treatment of Pauperism," 1893], but some accounts report certain older tramps would dominate a gay cat and employ him as a sort of slave. In "Sociology and Social Research" (1932-33) a paragraph on the "gay cat" phenomenon notes, "Homosexual practices are more common than rare in this group," and gey cat "homosexual boy" is attested in Noel Erskine's 1933 dictionary of "Underworld & Prison Slang" (gey is a Scottish variant of gay).

The "Dictionary of American Slang" reports that gay (adj.) was used by homosexuals, among themselves, in this sense at least since 1920. Rawson ["Wicked Words"] notes a male prostitute using gay in reference to male homosexuals (but also to female prostitutes) in London's notorious Cleveland Street Scandal of 1889. Ayto ["20th Century Words"] calls attention to the ambiguous use of the word in the 1868 song "The Gay Young Clerk in the Dry Goods Store," by U.S. female impersonator Will S. Hays, but the word evidently was not popularly felt in this sense by wider society until the 1950s at the earliest.

"Gay" (or "gai") is now widely used in French, Dutch, Danish, Japanese, Swedish, and Catalan with the same sense as the English. It is coming into use in Germany and among the English-speaking upper classes of many cosmopolitan areas in other countries. [John Boswell, "Christianity, Social Tolerance, and Homosexuality," 1980]

As a teen slang word meaning "bad, inferior, undesirable," without reference to sexuality, from 2000.

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