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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Honest Abe is forced to scheme, relying on grit and cunning to win the votes to abolish slavery.—
EW Staff Published,
EW.com,
4 July 2025 -
Of all the acts, though, Sudanese American vocalist Dua Saleh was the most subdued, swaying between heart-fluttering falsettos and cunning raps.—
Olivier Lafontant,
Pitchfork,
27 June 2025
Adjective
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Amazon has prevailed in a class-action lawsuit that accused it of engaging in deceptive trade practices.—
Will McCurdy,
PC Magazine,
19 July 2025
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Attorney General Phil Weiser’s office sent CBZ and its constituent companies several subpoenas in September as investigators probed the chronically unsafe conditions of the companies’ properties, as well as allegations from tenants that CBZ had engaged in insurance fraud and deceptive practices.—
Seth Klamann,
Denver Post,
16 July 2025
Adjective
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The moment in which Guy and Nan reunite at the courthouse and mirror each other on a staircase and over a railing, respectively, is reminiscent of their meet cute in Season 1.—
Dessi Gomez,
Deadline,
30 July 2025
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Make lunchtime fun again with the help of a cute and colorful bento box or a fun, interactive lunch box.—
Nora Colomer
may earn a commission if you buy through our referral links. This content was created by a team that works independently from the Fox newsroom.,
FOXNews.com,
30 July 2025
Adjective
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About 86% of the fraudulent claims for Medicare happened from December 2017 on.—
Meredith Colias-Pete,
Chicago Tribune,
29 July 2025
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An Arizona woman has been sentenced to more than eight years in prison for her role in a fraudulent scheme that helped North Koreans obtain remote IT positions at 309 US companies, including an unnamed member of the Fortune 500.—
Will McCurdy,
PC Magazine,
26 July 2025
Adjective
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The wine exhibits a delicate mousse featuring citrus-lime zest, layered with brioche, pear, and subtle minerality.—
Joseph V Micallef,
Forbes.com,
24 July 2025
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The combination adds layers of flavor and a subtle edge, giving the salsa the same flavor profile as a spicy version without any burn.—
Gabi De la Rosa,
Southern Living,
24 July 2025
Adjective
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The former Oakland Raiders linebacker was Arnold Schwarzenegger’s shady military pal in Predator (1987) before landing his own macho action vehicle in Action Jackson (1988).—
Skyler Trepel,
EW.com,
25 July 2025
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Visitors will find 2,000 miles of shady hiking trails, 3,000 ponds and lakes with water originating from cool mountain peaks, 30,000 miles of fresh and often chilly rivers and streams and millions of acres of sun-filtering forests.—
Matt Alderton,
USA Today,
24 July 2025
Adjective
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Republicans are right to be terrified with their prospects in November 2025 and 2026; there is going to be a major reckoning for their chaotic, crooked, and extreme governance.—
James Skoufis,
MSNBC Newsweek,
16 July 2025
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National reporters and true crime junkies dug in, while local officials — already lacquered in scandal — looked so crooked a frame job seemed not just possible but probable.—
Tom Blakely,
Boston Herald,
27 June 2025
Adjective
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Writing faculty have both the agency and the academic freedom to examine generative AI’s dishonest training origins and conclude: There is no path to ethically teach AI skills.—
Peter Greene,
Forbes.com,
22 July 2025
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So, in that moment, the things that are coming out of my mouth are not dishonest.—
Jason P. Frank,
Vulture,
22 July 2025
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Cite this Entry
“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 3 Aug. 2025.
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