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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As Michael moves into solo stardom and makes cunning business moves, the film captures how his seemingly naive idealism was also a form of ambition.—
Spencer Kornhaber,
The Atlantic,
24 Apr. 2026 -
Past friends and former associates described him to me as an exceptionally cunning con man, a consummate charmer, and a womanizer.—
Nate Freeman,
Vanity Fair,
3 Apr. 2026
Adjective
-
Guest reveals concerns about deceptive display.—
,
FOXNews.com,
28 Apr. 2026
-
Chicago arts venues are united in their disdain for the deceptive practice.—
Noel Brennan,
CBS News,
27 Apr. 2026
Adjective
-
Patagonian Scallops Tiny baby button scallops, so cute.—
Alex Beggs,
Bon Appetit Magazine,
25 Apr. 2026
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Someone says the rats are actually cute — what’s your honest response?—
Zach Schiffman,
Curbed,
24 Apr. 2026
Adjective
-
Legislators passed an emergency certification bill in February that increases fines for fraudulent redemption, requires redemption centers to keep track of bulk drop-offs and allows local police to go after out-of-state violators.—
Angela Eichhorst,
Hartford Courant,
30 Apr. 2026
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First, Jones submitted fraudulent expense reimbursement requests for fictitious business expenses.—
Irene Wright,
USA Today,
30 Apr. 2026
Adjective
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Brenden Aaronson could not finish a slick Leeds counter, denied by the outstretched boot of Robert Sanchez in the Chelsea goal.—
Beren Cross,
New York Times,
26 Apr. 2026
-
Pretty slick defensive play by the 2025 AL Platinum Glove recipient.—
Jaylon Thompson,
Kansas City Star,
26 Apr. 2026
Adjective
-
The campsites are nestled in a shady valley about a half-mile walk from the ferry port.—
Tribune News Service,
Baltimore Sun,
29 Apr. 2026
-
Nancy Pelosi found a shady spot under a tree.—
James Reginato,
Vanity Fair,
28 Apr. 2026
Adjective
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Throughout her trip to the United States, the Queen has reliably chosen British designers in a subtle showing of sartorial support of her homeland.—
Elise Taylor,
Vanity Fair,
29 Apr. 2026
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Such subtle tweaks in rhythm and resolution are more subtle, and more rewarding, than a straightforward joke-and-punchline setup.—
Alison Herman,
Variety,
29 Apr. 2026
Adjective
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The crooked lawyer, played by Bridget Regan, on ABC's police procedural series, died in the penultimate episode of Season 8 in a dramatic cliffhanger ahead of next week's finale.—
Anthony Robledo,
USA Today,
28 Apr. 2026
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The willow out front, where the children used to play, was thick and crooked with age.—
Lizzie Johnson,
New Yorker,
25 Apr. 2026
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Cite this Entry
“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 2 May. 2026.
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