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[gahyl-fuh l] /ˈgaɪl fəl/
insidiously cunning; artfully deceptive; wily.
Origin of guileful
Middle English word dating back to 1300-50; See origin at guile, -ful
Related forms
guilefully, adverb
guilefulness, noun
unguileful, adjective Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2018.
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Examples from the Web for guileful
Historical Examples
  • Why,” he added, with guileful simplicity, “you were wearing that very suit you have on now.

    The Law-Breakers Ridgwell Cullum
  • He had been soundly schooled by his guileful Sicilian mother.

    The Sea-Hawk Raphael Sabatini
  • He used every guileful ruse to cheat time of his determined moment.

    Sinister Street, vol. 1 Compton Mackenzie
  • He was the son of Bolverk, the son of Eyjolf the guileful, of Otterdale.

  • It seemed as if it could not be very deep or guileful, it was so frankly expressed.

    The Frontiersmen

    Charles Egbert Craddock
  • In passing and repassing it that evening, Rowena had vainly ransacked her guileful brain for an excuse to invade it.

  • Her approach was heralded by a note from Mr. Bainrothe, full of his characteristic, guileful sophistry and cool impertinence.

    Miriam Monfort Catherine A. Warfield
  • Abrupt frankness, with its guileful calculation to surprise one into betrayal, was the subtlest diplomacy.

    The Missourian

    Eugene P. (Eugene Percy) Lyle
  • Even as the Oriental he must be handled guilefully, and it was with a guileful yawn that I dismissed the subject.

    Margarita's Soul Ingraham Lovell
  • As he outlined his guileful proposition the scowls of his listeners gave way to grins of full approval and admiration.

    A Pagan of the Hills

    Charles Neville Buck
Word Origin and History for guileful

c.1300, from guile + -ful. Nowadays only in poems and dictionaries. Related: Guilefully; guilefulness.

Online Etymology Dictionary, © 2010 Douglas Harper
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