1
as in cunning
clever at attaining one's ends by indirect and often deceptive means
tried to fix the game with a guileful plot to sabotage the other team's bats, but the umpire caught them
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Antonyms & Near Antonyms
2
as in deceptive
given to or marked by cheating and deception
received a guileful answer when I asked the dealer if the used car had ever been in a collision
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Antonyms & Near Antonyms
Example Sentences
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Recent Examples of guileful
Bruno Guimaraes and Lucas Paqueta played guileful defence-splitting passes.
—
James Horncastle,
New York Times,
20 June 2026
One is to emphasize Iago—the guileful, insinuating convincingness of this malicious supervillain, who works on Othello to the point where any reasonable man would be deceived and fooled and worked into a rage that can lead to such a catastrophe.
—
David Frum,
The Atlantic,
17 June 2026
James Horncastle,
New York Times,
20 June 2026
One is to emphasize Iago—the guileful, insinuating convincingness of this malicious supervillain, who works on Othello to the point where any reasonable man would be deceived and fooled and worked into a rage that can lead to such a catastrophe.
—
David Frum,
The Atlantic,
17 June 2026
Recent Examples of Synonyms for guileful
Adjective
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That doesn't enable cunning and unprincipled men to subvert the power of the people.
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For decades, humans mined antibiotic molecules from microbes and tweaked them to develop new drugs, staying ahead of evolution’s cunning countermeasures.
Adjective
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Shadow fleet vessels disguise their identity and purpose through a broad range of deceptive activities, including spoofing their locations and destinations.
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The complaint alleged deceptive advertising and other misconduct.
Adjective
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Meanwhile, a cute side slit and practical pocket on the shorts add style and functionality.
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Join the droves of shoppers buying this cute henley top with a relaxed fit.
Adjective
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All three Republican candidates apparently hired the same signature gathering firm to collect signatures, many of which appear to have been fraudulent.
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However, because agentic systems can execute actions independently, an error can become a severe operational failure, such as authorizing fraudulent transactions or deleting mission-critical databases.
Adjective
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Off a slick feed from Houssem Aouar, Algeria’s Riyad Mahrez scored his second goal of the game to give Algeria a 3-2 lead.
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Appollis made some slick dribbles to set up a right-footed shot from outside the box.
Adjective
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The Italian-style grotto is a shady spot to visit on sunny days, with trees sheltering the pool and fountain.
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This woodland native grows in USDA Zones 6-9 and is best suited to shadier areas of the landscape.
Adjective
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Available in a style with the same stripes that Paltrow favors, the top offers a subtle pattern that’ll make your outfit pop.
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The square neckline adds a flattering, feminine touch, while the subtle volume in the sleeves gives it a slightly dressier feel than your average tee.
Adjective
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Warnock writes that his belief that the crooked places in America will be made straight keeps him motivated even on tough days at the Capitol.
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And ‘Meet the Press’ is crooked.
Cite this Entry
“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 3 Jul. 2026.
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