GUILEFUL Synonyms: 125 Similar and Opposite Words

guileful

adjective

Definition of guileful

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

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

Examples are automatically compiled from online sources to show current usage. Read More Opinions expressed in the examples do not represent those of Merriam-Webster or its editors. Send us feedback.

Recent Examples of guileful Bruno Guimaraes and Lucas Paqueta played guileful defence-splitting passes. — James Horncastle, New York Times, 20 June 2026 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

Recent Examples of Synonyms for guileful

Adjective

Sing, muse, of the cunning Christopher Nolan, who has once again achieved the impossible.

— Hillary Busis, Vanity Fair, 19 July 2026
In the classic tradition, this bit of strategic genius is the ultimate proof of Odysseus’s mētis, or cunning intelligence.

— Gal Beckerman, The Atlantic, 17 July 2026

Definition of cunning

Adjective

The standout interlude is the soldiers’ visit to the island domain of Circe, a treacherous witch played with deceptive calm and a misleading air of distraction by a bone-chilling Samantha Morton.

— David Rooney, HollywoodReporter, 15 July 2026
Using a clinician’s name, image, or credentials in a synthetic endorsement without consent should be treated as deceptive practice, with liability directed toward those who commission or distribute the content.

— Henry Bair, STAT, 14 July 2026

Definition of deceptive

Adjective

Sherri Shepherd looks cute in polka dots to watch Tracee Ellis Ross make her Broadway debut in Every Brilliant Thing on July 16 in New York City.

— People Staff, PEOPLE, 18 July 2026
Meredith, New Hampshire Meredith is one of those almost unbearably cute small East Coast towns—especially in the fall, when the colors really pop.

— Evie Carrick, Travel + Leisure, 17 July 2026

Definition of cute

Adjective

Bruneau moved in with her boyfriend and told her family that Larry Brown was pressuring her to sign fraudulent insurance documents with inflated repair costs, according to the affidavit.

— Amy McDaniel, Fort Worth Star-Telegram, 16 July 2026
Keep records of all communications and fraudulent transactions.

— Brian Sloan,Dan Avery, CNBC, 15 July 2026

Definition of fraudulent

Adjective

Noe negotiated with Li Shan in a pidgin mix of French, English, and Cantonese as the workers fanned out on the wobbling platform, slipping on the slick bodies and shells of the catch.

— Literary Hub, Literary Hub, 16 July 2026
None This finding is a bit more in line with conventional sabermetrics wisdom, which holds that pitchers who dominate the strike zone have better long-term outcomes than those who rely on stranding runners and asking for slick fielding behind them.

— Neil Paine, New York Times, 16 July 2026

Definition of slick

Adjective

Debbie, named after Coates’ mother, feels betrayed by Judith and her husband, who is involved in shady dealings with an Albanian gang.

— Emily Zemler, Los Angeles Times, 16 July 2026
But the story about the war hero Odysseus, whose journey home with his men is beset by sea storms, shipwrecks, gods, monsters and shady ladies, set the template for literature, comic books, science fiction and Hollywood epics for centuries to come.

— Jim Beckerman, USA Today, 16 July 2026

Definition of shady

Adjective

But Scheft and his team are mastering the subtle differences and plan to offer many of the same loaves available in Boston, though the bakeries will have a few different offerings.

— Connie Ogle July 17, Miami Herald, 17 July 2026
In one of Nolan’s subtle but important additions to Homer’s tale, all throughout the film, everyone expresses fears about the People from the Sea, this unseen menace terrorizing different towns.

— Bilge Ebiri, Vulture, 17 July 2026

Definition of subtle

Adjective

Resurrection Dex’s Resurrection is an uncomfortably honest and self-critical mixtape about the British rapper attempting to reform his crooked ways.

— Alphonse Pierre, Pitchfork, 17 July 2026
Whitehead, meanwhile, crystalizes his sense of what makes the city run, where Carney fits in, and how the straight and crooked worlds are entwined in one strange ecosystem with laws that only the lawless can enforce.

— David Hajdu, The Atlantic, 16 July 2026

Definition of crooked

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“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 22 Jul. 2026.

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Synonyms of guileful

adjective

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