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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Köhler specializes in cunning, tonally surprising films about cross-cultural disconnection, and Gavagai is his most ambitious and expansive film yet—a pinpoint-accurate account of moral crises and social biases, modern and ancient, internal and external.—
Jill Goldsmith,
Deadline,
5 Aug. 2025 -
But as the supervisors tweaked the incentives, a new form of cunning arose.—
Craig S. Smith,
Forbes.com,
25 July 2025
Adjective
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These emails are loaded with deceptive links that lead to malware infections, and the consequences can be severe.—
Kurt Knutsson,
FOXNews.com,
14 Aug. 2025
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Match Group, the parent company of Match.com, Tinder, Hinge, OkCupid, and PlentyOfFish, has agreed to pay $14 million to settle a complaint with the Federal Trade Commission about deceptive advertising practices.—
Chris Morris,
Fortune,
13 Aug. 2025
Adjective
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The trailers for the episode dropped not only the announcement of Swift's latest album, but also a cute moment between the celeb couple.—
Joyce Orlando,
Nashville Tennessean,
12 Aug. 2025
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The brand also offers the pillow in a smaller base model and several cute kids’ pillows that double as plushies.—
Clint Davis,
People.com,
11 Aug. 2025
Adjective
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Candidates flagged for fraudulent behavior had a 27% lower quality of hire than their honest peers, according to the same study.—
Michael Fitzsimmons,
Forbes.com,
8 Aug. 2025
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Jones was charged with three felonies — theft of a credit card, criminal use of personal identification information, and fraudulent use of a credit card over two times within six months, the Tallahassee Democrat reported.—
Angel Saunders,
People.com,
8 Aug. 2025
Adjective
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The change was subtle enough that most legislators missed it.—
Orlando Sentinel Editorial Board,
The Orlando Sentinel,
5 Aug. 2025
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The sleeveless ensemble features a pink and yellow pattern with subtle baby blue and neon yellow accents.—
Catherine Santino,
People.com,
5 Aug. 2025
Adjective
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On bright sunny days in summer, look for a shady place where light intensity is reduced.—
Anthony A. Ciuffa,
Outdoor Life,
7 Aug. 2025
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Once they’ve been admitted, users have access to profiles of men annotated with information such as background checks and dating reviews; men with shady dating histories are rated with red flags.—
Kyle Chayka,
New Yorker,
6 Aug. 2025
Adjective
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The radio-wavelength image shows that the black hole’s jet is not straight, but is crooked with three distinct bends.—
Keith Cooper,
Space.com,
1 Aug. 2025
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In one image, Scales, who had won a Military Cross for his bravery at the front, wears a crooked grimace that suggests recent anguish.—
Ed Caesar,
New Yorker,
13 July 2025
Adjective
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At the heart of Trump’s complaints is a familiar refrain: The media is not only biased, but dishonest, corrupt and dangerous.—
Stephanie A,
The Conversation,
4 Aug. 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 19 Aug. 2025.
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