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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In state media comedy shows, jokes about Putin are told from time to time, but they are used to bolster his image as a powerful, cunning leader, and hold up Russia as a great country.—
Neringa Klumbytė,
The Conversation,
4 Mar. 2026 -
These ambitious, cunning, and often amoral Cold War operatives were usually marginal or even inconsequential figures at home.—
Alfred McCoy,
Literary Hub,
26 Feb. 2026
Adjective
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In the short term, the company focuses on immediate relief from rising annual maintenance fees, open loans, and the financial fallout from deceptive sales practices.—
Malana VanTyler,
USA Today,
9 Mar. 2026
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Tenet had sued Leapfrog last year over poor grades given to its Palm Beach Network hospitals, calling the grading process unfair and deceptive.—
Cindy Krischer Goodman,
Sun Sentinel,
9 Mar. 2026
Adjective
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This cute mini skort can be worn with any top already in your wardrobe, or with the Gap crop tank top as a matching set.—
Caroline Hughes,
Travel + Leisure,
8 Mar. 2026
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The idea of putting a cute sticker on your body every day to take a supplement seems fun in theory.—
Korin Miller,
SELF,
6 Mar. 2026
Adjective
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California has paid roughly $20 billion in fraudulent unemployment benefits to scammers, about 11% of all benefits distributed since the beginning of the COVID-19 pandemic, state officials said this week.—
Hannah Fry,
Los Angeles Times,
6 Mar. 2026
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Over a 14-year period from 2012 to 2016, hundreds of thousands of Wells Fargo’s Community Bank employees opened millions of unauthorized or fraudulent accounts and other financial products to meet excessive sales goals.—
Charlotte Observer,
Charlotte Observer,
5 Mar. 2026
Adjective
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Jared Wright skated it down and turned back a slick pass for Laughton, whose whirling, sharp-angle bid beat Dobeš improbably to the far side.—
Andrew Knoll,
Daily News,
8 Mar. 2026
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In the end, such planning was rendered redundant by a combination of VAR and slick Chelsea play in extra time, leaving Wrexham to focus on perhaps making this fixture an annual event in the Premier League.—
Richard Sutcliffe,
New York Times,
8 Mar. 2026
Adjective
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So forget shady characters, or fake websites.—
Dave Lieber
Mar. 11,
Dallas Morning News,
11 Mar. 2026
-
The inspiration for this pasta comes from the shady, mysterious forests of Northern California’s Redwood National and State Parks.—
John Metcalfe,
Mercury News,
11 Mar. 2026
Adjective
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Among California’s most upscale neighborhoods, a subtle reshuffling has taken place in recent decades, with the highest home values migrating from Northern California to Southern California.—
Terry Castleman,
Los Angeles Times,
12 Mar. 2026
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Key Takeaways The symptoms of transthyretin amyloid cardiomyopathy (ATTR-CM)—a disease of the heart muscle—are often subtle and can mimic those of other heart conditions, especially in the early stages.—
Colleen Doherty,
Verywell Health,
11 Mar. 2026
Adjective
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And no more crooked mail-in ballots except for illness, disability, military or travel, none.—
Irene Wright,
USA Today,
27 Feb. 2026
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And no more crooked mail-in ballots except for illness, disability, military, or travel.—
TIME Staff,
Time,
25 Feb. 2026
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Cite this Entry
“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 12 Mar. 2026.
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