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Oxymoron

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lankeela | 18:23 Mon 31st Jul 2006 | Phrases & Sayings
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Why do we say someone or something is pretty ugly?

And why do we say pretty bad or pretty good, or even pretty much?
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World Wide Words has this to say:
That�s correct. It is first recorded in Old English, when it had the sense of �trick, deceit�. Then it disappears from the recorded language for some centuries, turning up again in the 1400s in a variety of meanings, none of them exactly equivalent to the Old English form. It could mean �clever, artful�, or �something ingeniously or cleverly made�.

Contd.
Contd. (site still won't take longer posts, apparently)

And it could be applied to a man, as �brave, gallant, warlike�, which weakened down the years until it was used in the eighteenth century in the phrase �a pretty fellow�, meaning a swell or a fop. But the word also existed in a weakened sense, very much like our modern nice�pleasing or satisfactory in a vague sort of way. In this sense it was applied, in rather a condescending way, to young women as a reduced version of beautiful.

ObvIously, as the word aged the meaning became useful in producing oxymorons such as yours...
These days "pretty" in this context means much the same as very only a bit less so. By the way, only the first one (pretty ugly) is an oxymoron - pretty good and pretty bad are not.

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