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
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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
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Recent Examples of guileful
One is to emphasize Iago—the guileful, insinuating convincingness of this malicious supervillain, who works on Othello to the point where any reasonable man would be deceived and fooled and worked into a rage that can lead to such a catastrophe.
—
David Frum, The Atlantic, 17 June 2026
David Frum, The Atlantic, 17 June 2026
Recent Examples of Synonyms for guileful
Adjective
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Daemon is one of the most clever, cunning and conniving characters in House of the Dragon, who always seems to have the upper hand.—
Skyler Trepel,
PEOPLE,
22 June 2026
-
Under this light, Penelope emerges as exemplary, cunning, wounded, and trapped by the male order that praises her.—
David Denby,
New Yorker,
21 June 2026
Adjective
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The suit alleges the group, known widely as WPATH, made deceptive claims about gender-affirming care for minors and that its members profited off the claims.—
ABC News,
ABC News,
17 June 2026
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Grand Canyon’s rim-to-river routes can be deceptive because the steepest physical test comes on the way out, after hikers have descended into hotter terrain, experts say.—
Jessica Mekles,
FOXNews.com,
15 June 2026
Adjective
-
Serve this sweet-and-spicy salad with your favorite cute cocktail picks for a fresh-and-fun summer appetizer.—
Lisa Cericola,
Southern Living,
20 June 2026
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Baby raccoons, for example, are very cute, but their mother may have made a den in the attic, crawl space, or shed, which can be bad for them and for the homeowner.—
Michelle Mastro,
Martha Stewart,
20 June 2026
Adjective
-
The guardian approved fraudulent time sheets, and Davis paid the guardian kickbacks, the release says.—
Arkansas Online,
Arkansas Online,
18 June 2026
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And in late 2025, Grady took on Meta (formerly called Facebook), including its affiliates Instagram and Whatsapp, for allowing fraudulent Chinese investment scams on its platforms.—
Shirsho Dasgupta,
Miami Herald,
18 June 2026
Adjective
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Tolbert also made a slick play to end the game.—
Blair Kerkhoff,
Kansas City Star,
20 June 2026
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Much like his longstanding working relationships with BlocBoy JB and Sexyy Red, Tay Keith also had a similar footing with Drake, providing the soundscape for some of the 6 God’s slickest sneak disses.—
DeMicia Inman,
VIBE.com,
20 June 2026
Adjective
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Although some mushrooms tolerate sun, mushrooms are more likely to sprout in shady spots with lots of overhanging trees and brush.—
Lauren Landers,
The Spruce,
16 June 2026
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However, if the area is shady and soggy, a groundcover may be the best choice if drainage issues cannot be remedied.—
Mary Marlowe Leverette,
Southern Living,
16 June 2026
Adjective
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Star power takes a neutral cat-eye base and turns it into a subtle statement moment.—
Amanda Le,
InStyle,
17 June 2026
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Where their Florida style is bold and flamboyant, the ranch is subtle and defined by a rich, earthy palette.—
Elizabeth Kiefer,
Architectural Digest,
17 June 2026
Adjective
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Warnock writes that his belief that the crooked places in America will be made straight keeps him motivated even on tough days at the Capitol.—
Tia Mitchell,
AJC.com,
15 June 2026
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And ‘Meet the Press’ is crooked.—
Los Angeles Times,
Los Angeles Times,
15 June 2026
Cite this Entry
“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 24 Jun. 2026.
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