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guileful

American  
[gahyl-fuhl] / ˈgaɪl fəl /

adjective

  1. insidiously cunning; artfully deceptive; wily.


Other Word Forms

Etymology

Origin of guileful

Middle English word dating back to 1300–50; see origin at guile, -ful

Example Sentences

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

See Examples For:

Ms. Jackson is no apologist—her James has flaws aplenty—but where prior historians offered snide caricature, she portrays a complex leader who was “intelligent, resilient, idiosyncratic, irascible, guileful and witty.”

From The Wall Street Journal Dec. 5, 2025

Creepy Santa never gets his ultimate comeuppance, guileful Snow White never finds her ideal prince.

From Los Angeles Times Feb. 18, 2020

Equally enjoyable is the pleasure, borrowed from John le Carré, of watching the games of vastly intelligent and dead-hearted men as they play with the lives of the less guileful.

From New York Times Feb. 11, 2020

Facebook’s own guileful way of presenting the issue was to claim that while “passive” consumption of social media content could pose mental health risks, more engagement could “improve wellbeing”.

From The Guardian Aug. 23, 2019

And however much they played and were children, still their faces were scored with the knowledge and cares that children should not have, their eyes were knowing and guileful beyond their years.

From "Nectar in a Sieve" by Kamala Markandaya

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