Entries linking to pretty-boy
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.
mid-13c., boie "servant, commoner, knave" (generally young and male); c. 1300, "rascal, ruffian, knave; urchin," mid-14c. as "male child before puberty" (possibly an extended sense from the "urchin" one). A word of unknown origin.
Possibly from Old French embuie "one fettered," from Vulgar Latin *imboiare, from Latin boia "leg iron, yoke, leather collar," from Greek boeiai dorai "ox hides." (Words for "boy" double as "servant, attendant" across the Indo-European map -- compare Italian ragazzo, French garçon, Greek pais, Middle English knave, Old Church Slavonic otroku -- and often it is difficult to say which meaning came first.)
But it also appears to be identical with East Frisian boi "young gentleman," and perhaps with Dutch boef "knave," from Middle Dutch boeve, perhaps from Middle Low German buobe. This suggests a gradational relationship to babe. For a different conjecture: Used slightingly of young men in Middle English, also in familiar or contemptuous use of criminal toughs or men in the armed services. In some local uses "a man," without reference to age (OED lists "in Cornwall, in Ireland, in the far West of the U.S."). Meaning "male negro slave or Asian personal servant of any age" attested from c. 1600. Extended form boyo is attested from 1870. Emphatic exclamation oh, boy is attested by 1917. Boy-meets-girl "typical of a conventional romance" is from 1945; the phrase itself is from 1934 as a dramatic formula. Boy-crazy "eager to associate with males" is from 1923.
In Old English, only the proper name Boia has been recorded. ME boi meant 'churl, servant' and (rarely) 'devil.' In texts, the meaning 'male child' does not antedate 1400. ModE boy looks like a semantic blend of an onomatopoeic word for an evil spirit (*boi) and a baby word for 'brother' (*bo). [Liberman]
A noticable number of the modern words for 'boy', 'girl', and 'child' were originally colloquial nicknames, derogatory or whimsical, in part endearing, and finally commonplace. These, as is natural, are of the most diverse, and in part obscure, origin. [Buck]