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
Relevance
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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While people born in the year of the snake are seen as charismatic, intelligent, and artistic, they are also often considered cunning and mysterious.—
Saman Shafiq,
USA Today,
16 Feb. 2026 -
And Halston has a cunning plan.—
Kaycee Sloan,
Cincinnati Enquirer,
13 Feb. 2026
Adjective
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Not sharing news of the increase was deceptive, and the company should be fined.—
Dave Lieber,
Dallas Morning News,
18 Feb. 2026
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The agency also alleged other deceptive practices.—
James Powel,
USA Today,
18 Feb. 2026
Adjective
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Real Arizonans know that Valentine's Day is so much more than an excuse for candy and cute notes.—
Becky Bartkowski,
AZCentral.com,
14 Feb. 2026
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From workplace romances to relationships built from body horror events, these are the precious pairs encouraging everyone to choose love above all and make that cute hand heart gesture.—
Sergio Pereira,
Space.com,
14 Feb. 2026
Adjective
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Trauernicht, the former fire chief, allegedly approved numerous fraudulent paychecks for his female assistant.—
Rosalio Ahumada,
Sacbee.com,
19 Feb. 2026
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If convicted, the suspects will have to forfeit to the government any property purchased with proceeds from the fraudulent cattle deals.—
Harriet Ramos,
Fort Worth Star-Telegram,
19 Feb. 2026
Adjective
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The singer completed the look with a bold snake choker necklace and a super slick bun.—
Meg Walters,
InStyle,
15 Feb. 2026
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When skin starts feeling slick or congested, Medicube’s Zero Pore Pads help restore balance.—
Christa Joanna Lee,
Allure,
15 Feb. 2026
Adjective
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What, is something shady happening?—
Alice Burton,
Vulture,
16 Feb. 2026
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Richards counterattacked Mattox, hinting he’d been involved in shady deals and challenging his ethics and finances.—
Gromer Jeffers Jr,
Dallas Morning News,
16 Feb. 2026
Adjective
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Two brands – one, Diotima, led by female designer Rachel Scott, and the other, Eckhaus Latta, by Mike Eckhaus and Zoe Latta – showed a subtler way to get fashion audiences thinking.—
Rachel Tashjian,
CNN Money,
18 Feb. 2026
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The muted denim blue creates a subtle pop of color, and the large medallion pattern in the center is distressed for an antique feel.—
Shea Simmons,
Southern Living,
18 Feb. 2026
Adjective
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More than half a million residents live in NYCHA development plagued by chronic mold, broken elevators, and heating failures; others reside in subpar tenements run by crooked landlords.—
Darius Jones,
New York Daily News,
15 Feb. 2026
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The company was ripped off over and over in more than 100 crooked transactions, the agreement said.—
Steve Patterson,
Florida Times-Union,
10 Feb. 2026
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Cite this Entry
“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 21 Feb. 2026.
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