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fredpuli47 | 20:09 Sat 23rd Oct 2010 | Word Origins
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We think now of 'pretty' as 'pleasing to the eye' but we also say 'pretty' in 'pretty good', 'pretty tough' and so on, and once said that something cost 'a pretty penny' meaning 'a lot of money'. When did these uses of 'pretty' come into English ?
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Pretty meaning considerable first appeared in the late 15th century...a pretty while, a pretty way off and a pretty deal, for example, had all appeared by the mid 1500s. A pretty penny is first recorded in 1712 in an essay by Steele in the Spectator.
Q, as usual has presented a stentorian reply... it may be of value to understand the devlopment of the word 'pretty'...

O.E. prættig (W.Saxon), *prettig (Mercian) "cunning, skillful, artful," from prætt, *prett "a trick, wile, craft," from W.Gmc. *pratt- (cf. O.N. prettr "a trick," prettugr "tricky;" Fris. pret, M.Du. perte, Du. pret "trick, joke," Du. prettig "sportive, funny," Flem. pertig "brisk, clever"). Connection between O.E. and M.E. words is uncertain, but if they are the same, meaning had shifted by c.1400 to "manly, gallant," and later moved via "attractive, skillfully made," to "fine," to "beautiful in a slight way" (mid-15c.). For sense evolution, compare nice, silly. Used to qualify adjectives and adverbs ("moderately") since 1560s. As a verb (usually with up) it is attested from 1916. Prettily is from c.1400; prettify first recorded 1850. Pretty-boy is attested from 1885. A pretty penny "lot of money" is first recorded 1768. (Source: Online Etymology Dictionary)
Sorry all,cannot keep pace with such highly educated replies.
Mind you I may never know when Clanads reply may come in handy.
All I wanted to say re.the word pretty,was that,when I hear the phrase "pretty please"
usually said to a woman,by a man,I find it derogatory and unnecessary.
Our friends at Word Detective" tend to agree with you, daftgrandad:

"Pretty please” is a phrase used, as the Oxford English Dictionary notes,”in emphatically polite or imploring request[s].” “Pretty please with sugar on top” is Extra Strength Pretty Please, deployed by children and desperate adults in an appeal for cooperation when all other entreaties have failed.

Plain old “please” used in requests (”Please send money”) is an adverb, based on the verb “to please” meaning “to be agreeable or pleasant,” derived from the Latin “placere” (”to be pleasant”). The “request” use of “please” probably originated as a shortened form of the phrase “if it pleases you [to do whatever].”

“Pretty” primarily means, of course, “attractive,” and is rooted in the Old English “praettig,” which meant “clever.” In the 16th century, “pretty” came into use as an adverb meaning “to a considerable extent” (”Bob’s pretty sick”) or, as an adjective, “substantial” (”That boat must have cost a pretty penny”). In the phrase “pretty please,” “pretty” functions as an intensifier, ratcheting up the strength of the “please” to signify that the speaker really, really wants whatever it is they’re asking for. “With sugar on top” turns the urgency dial up to eleven.

The earliest citation in the Oxford English Dictionary for “pretty please” is from 1913, and the earliest for “pretty please with sugar on top” is from 1973. But my guess is that “with sugar on top” actually arose much earlier, at least by the 1950s. While sprinkling sugar on food has a long history, it was in the 1950s when ready-made sugar-coa
The part that was cutoff (due to length, I suspect) reads as follows:

"...breakfast cereal became popular, and the phrase may have been spawned then in imitation of advertising (”Ask Mom for Choco-Balls — the ones with with sugar on top!”) for such wholesome fare.

“Pretty please with sugar on top” was always a bit excessive coming from a child, and on the lips of an adult is often meant as sarcasm, as in Quentin Tarantino’s film Pulp Fiction, where a character says, “I need you guys to act fast if you want to get out of this. So pretty please, with sugar on top, clean the [bleeping] car.”
Thanks Clanad for that.
Unfotunately could,nt finish reading all,as I was losing the will to live.
Thanks for that Clanad.

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