guileful

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.

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

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

He was never truthful with anyone, but always guileful in what he said and did, yet easily hoodwinked by any who wanted to deceive him.

From Textbooks • Jan. 1, 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