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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Fueled by vengeance and cunning ambition, Ashur rises from betrayal and bloodshed to seize power, gouging out a place for the House of Ashur in a new arena full of violence, desire, and twisted loyalty.—
Rosy Cordero, Deadline, 30 Oct. 2025
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The elaborate scheme, masterminded by members of four Mafia families in collusion with celebrity athletes, ensnared unsuspecting victims, bleeding them of over $7 million through cunning deception, prosecutors said in the indictment.—
Adjective
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While not everyone gets their wishes, those with no interest in taking on the deceptive — and challenging — role of a Traitor likely won't be chosen.—
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The legal claims included negligence, wrongful death, deceptive trade practices, and product liability.—
Adjective
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Ariana Grande made a cute face while taking a pic with Steven Spielberg.—
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Jump on the trend early with this cute, hands-free Michael Kors crossbody bag.—
Adjective
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From May 2020 to January 2022, Vazquez, Highsmith and several associates submitted fraudulent applications to financial institutions and the Small Business Administration.—
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Trauernicht, 46, is accused of approving McFadden’s fraudulent timesheets while seeking a romantic relationship with her.—
Adjective
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The slick material keeps chafing to a minimum during workouts, and the brushed inside is so soft against the skin and helps keep cold air out and your body heat in.—
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Between the melting ice under the court and heavy rain Thursday night in Chicago, condensation created a slick and dangerous playing surface.—
Adjective
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The bill is meant to explicitly prohibit that kind of shady transaction.—
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As would giving Law an award for playing a shady restaurateur in Black Rabbit.—
Adjective
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With her signature long waves gathered into a subtle bun at the nape of her neck, this style puts the focus on the sculptural wave framing Seyfried's face opposite a deep side part.—
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Grande wore a glossy pink shade on her lips, sculpted cheeks with subtle shimmer, and long lashes.—
Adjective
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Willms plans to call the Bureau of Land Management — the agency that oversees these parcels of federal land — to report the crooked stake.—
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Begin by removing any suckers at the base of the tree, side shoots on the trunk, crossing or crooked branches, dead or damaged branches, those that are growing inward, and crowded branches.—
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Cite this Entry
“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 13 Jan. 2026.
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