guileful

adjective

Definition of guilefulnext
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

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
  1. cunning
  2. deceptive
  3. cute
  4. fraudulent
  5. slick
  6. shady
  7. subtle
  8. crooked
Adjective
  • Magpies are opportunistic scavengers, incredibly cunning and deceitful and capable of calculated deception.
    — Voice of the People, New York Daily News, 28 Sep. 2026
  • Last week, Alan Cumming’s cunning competition empire The Traitors unsheathed its most diabolical twist yet.
    — Rebecca Alter, Vulture, 24 Sep. 2026
Definition of cunning
Adjective
  • In past elections, deceptive political robocalls have resulted in significant fines associated with the Telephone Consumer Protection Act, the federal law at the center of the petition.
    — ABC News, ABC News, 7 Oct. 2026
  • The film chronicled Gortner’s youth as a Pentecostal preacher in the American South and exposed the deceptive practices used to bilk believers out of their money.
    — Greg Evans, Deadline, 6 Oct. 2026
Definition of deceptive
Adjective
  • As a woman waded through the waters around the Bridge Side Marina in Bridge Isle, Louisiana, the tiny canine with a fluffy white coat wiggled his forelegs as if swimming, video of the cute moment shows.
    — Erika Angulo, NBC news, 11 Oct. 2026
  • The actress, who lends her voice to the fictional pop star Venus Nova in the film, sported a cute pair of strappy shoes that appear to be Manolo Blahnik’s Leva 105 Sandal.
    — Erin Wisti, Footwear News, 10 Oct. 2026
Definition of cute
Adjective
  • Prosecutors allege the crew printed fraudulent UPS labels to reroute boxes nationwide.
    — Glenn Taylor, Footwear News, 8 Oct. 2026
  • Rush’s fraudulent conduct cost the federal government approximately $194 million in total losses, according to the Justice Department.
    — Michael Kunzelman, Los Angeles Times, 7 Oct. 2026
Definition of fraudulent
Adjective
  • That calculation is pushing retail technology toward fitting-room innovation rather than slick checkout flows alone.
    — Lauren Schuster, Charlotte Observer, 8 Oct. 2026
  • It’s paired with a blend of lightweight sunflower, olive, and jojoba oils that melt down makeup, sunscreen, and excess sebum without leaving skin feeling slick or weighed down.
    — Christa Joanna Lee, Allure, 7 Oct. 2026
Definition of slick
Adjective
  • The extensive wellness area is built into the rocks with a series of open-air mezzanines, treatment rooms, shady sea-viewing spots and plunge pools.
    — Condé Nast, Condé Nast Traveler, 8 Oct. 2026
  • Aside from Anderson, Paz and Méndez have moments of raw emotion in their scenes together, but Affleck and Washington never generate much heat, while Yeun mostly stands around looking shady.
    — David Rooney, HollywoodReporter, 8 Oct. 2026
Definition of shady
Adjective
  • Poindexter featured his three daughters in his first campaign advertisement for the general election, taking a subtle dig at Miller.
    — Lauren Green, The Washington Examiner, 7 Oct. 2026
  • Later still, we are introduced to Satoko Iijima (Ishida), who again shares many defining features with her two namesakes, albeit with just enough subtle differences to keep the audience on the back foot.
    — James Marsh, Variety, 7 Oct. 2026
Definition of subtle
Adjective
  • Others convicted in relation to the robbery included Brian Reader, a career criminal who was involved in other high-profile robberies before and after Brink’s-Mat, crooked solicitor Michael Relton, and McAvoy’s wife, Kathleen.
    — Frannie Comstock, Encyclopedia Britannica, 9 Oct. 2026
  • For now, the crooked finger stays, and so does the jumper that comes with it.
    — Kristian Winfield, New York Daily News, 1 Oct. 2026
Definition of crooked

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Cite this Entry

“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 15 Oct. 2026.

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