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
Synonyms & Similar Words
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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
Synonyms & Similar Words
Antonyms & Near Antonyms
Example Sentences
Recent Examples of Synonyms for guileful
Adjective
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What could be more cunning and disgusting than training dogs to commit anal rape?—
David Frum,
The Atlantic,
21 May 2026 -
Dano’s static line delivery gets used for a chilling but laconic effect as his character’s cunning political negotiations lead to deadly outcomes.—
Randy Myers,
Mercury News,
13 May 2026
Adjective
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This isn’t an easy history to tell since obfuscation, confusion, and deceptive hype are its central themes.—
Jonathan Odden,
Artforum,
2 June 2026
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Owens also challenged the ballot title and summary as deceptive.—
Jack Harvel
June 2,
Kansas City Star,
2 June 2026
Adjective
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Keep scrolling to start the season strong with ’90s-but-better jelly mules, cute lightweight dresses, and a sling bag that’s about to become your water bottle’s new best friend.—
Annie Blackman,
InStyle,
6 June 2026
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Bonus points for picking separates in the same color palette (red and white is a particularly cute, preppy combo, as shown above).—
Kelsey Stewart,
Glamour,
6 June 2026
Adjective
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Holmes fashioned herself as the next Steve Jobs, until a reporter at the Wall Street Journal blew the lid off Theranos' fraudulent claims of developing a state-of-the-art medical test that required only a single drop of blood to accurately detect results like glucose levels and cancer.—
James Mercadante,
Entertainment Weekly,
4 June 2026
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The Justice Department alleges the two businesses submitted fraudulent claims for services that were never rendered.—
Luke Barr,
ABC News,
4 June 2026
Adjective
-
Junior Brooke Neale applied a slick tag.—
Dan Albano,
Oc Register,
31 May 2026
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But homes are personal spaces, and consumers will need more than a shiny robot and a slick app.—
Kurt Knutsson,
FOXNews.com,
31 May 2026
Adjective
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As your seedlings start to grow, trim each pot down to one seedling before exposing them to the outdoor environment in a shady spot for a few hours everyday for at least a week.—
Ashlyn Needham,
Southern Living,
2 June 2026
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Matsui campaign strategist Roger Salazar clapped back against the allegations of shady PAC spending Friday, pointing to super PAC spending on Vang’s behalf.—
Jennah Pendleton,
Sacbee.com,
1 June 2026
Adjective
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The collection is highly versatile, offering both subtle nods to the sport and head-to-toe outfits, all created in a patriotic color palette of red, white and a variety of blues.—
Kelsey Legg,
ABC News,
3 June 2026
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The actress, also known for Todd Haynes' film May December, later comments on that subtle addition in a May 2026 interview.—
Entertainment Weekly,
Entertainment Weekly,
3 June 2026
Adjective
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The set design is intricate and distorted—visible paintbrush strokes, acute angles, crooked lines—lending the film a surreal quality and supporting its cast of expressive actors, exaggerated costuming, and eerie makeup.—
Air Mail,
Air Mail,
30 May 2026
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Falter struggled, but he also wasn’t helped by a replay review that helped the Yankees put up a crooked number in the first inning.—
Pete Grathoff,
Kansas City Star,
27 May 2026
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Cite this Entry
“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 7 Jun. 2026.
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