Dictionary.com
Thesaurus.com
Synonyms

guileful

American  
[gahyl-fuhl] / ˈgaɪl fəl /

adjective

  1. insidiously cunning; artfully deceptive; wily.


Other Word Forms

  • guilefully adverb
  • guilefulness noun
  • unguileful adjective

Etymology

Origin of guileful

Middle English word dating back to 1300–50; 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.

In fact her quote was more guileful than that—and all the more revealing for it.

From The Wall Street Journal • Oct. 20, 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

She had the sort of broad and guileful smile in which you couldn't help but believe—you just wanted to make her happy so you could keep seeing it.

From "An Abundance of Katherines" by John Green