Etymology
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wile (v.)
late 14c., "to deceive," from wile (n.). Related: Wiled; wiling. Sense of "cause (time, etc.) to pass pleasantly, divert attention pleasantly" is by 1796, from confusion with while (v.).
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wile (n.)
late Old English, wil "stratagem, trick, sly artifice," perhaps from Old North French *wile (Old French guile), or directly from a Scandinavian source (compare Old Norse vel "trick, craft, fraud," vela "defraud"). Perhaps ultimately related to Old English wicca "wizard" (see Wicca). Lighter sense of "amorous or playful trick" is from c. 1600.
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wily (adj.)
"subtle, cunning, crafty," early 14c., from wile (n.) + -ly (1). Related: Wiliness. In 16c. English had wily-pie "cunning fellow."
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while (v.)
"to cause (time) to pass (without dullness)," 1630s, earlier "to occupy or engage (someone or something) for a period of time" (c. 1600), new formation from while (n.), not considered to be from Middle English hwulen "to have leisure," which is from a Germanic verb form of while (n.) (compare German weilen "to stay, linger"). An association with phrases such as Shakespearean beguile the day, Latin diem decipere, French tromper le temps "has led to the substitution of WILE v by some modern writers" [OED] (see wile (v.)).
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fox (v.)
1660s, "to delude" (perhaps implied in Old English foxung "fox-like wile, craftiness"), from fox (n.). The same notion is implied in Old English verbal noun foxung "fox-like wile, craftiness;" and Middle English had foxerie "wiliness, trickery, deceit." Foxed in booksellers' catalogues (1847) means "stained with fox-colored marks" (rusty red-brown). In other contexts the past-participle adjective typically meant "drunk" (1610s).
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guile (n.)
mid-12c., from Old French guile "deceit, wile, fraud, ruse, trickery," probably from Frankish *wigila "trick, ruse" or a related Germanic source, from Proto-Germanic *wih-l- (source also of Old Frisian wigila "sorcery, witchcraft," Old English wig "idol," Gothic weihs "holy," German weihen "consecrate"), from PIE root *weik- (2) "consecrated, holy."
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*ser- (1)

Proto-Indo-European root meaning "to protect." It forms all or part of: conservation; conservative; conserve; observance; observatory; observe; preserve; reservation; reserve; reservoir.

It is the hypothetical source of/evidence for its existence is provided by: Avestan haurvaiti "to guard;" Latin servare "to guard, keep, watch;" Old Church Slavonic xraniti "to guard, protect;" Old High German gi-sarwi "armor, equipment," Old English searu "art, skill; wile, deceit."

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drunken (adj.)

full form of the past participle of drink. Now chiefly as an adjective, "inebriated;" that sense was in Old English druncena. The meaning "habitually intoxicated" is by 1540s. Also, of things, "soaked, saturated" (early 15c.). Figurative sense of "acting as if drunk, uneven, unsteady" is by 1786.  Related: Drunkenly. In the sense "addicted to drink, habitually inebriated" Middle English also had drunc-wile (c. 1200); drunkensom (mid-13c.).

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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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