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

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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
  • Consider, for instance, the institution of oprichnina that Tsar Ivan IV established in 1565, through various cunning moves.
    — Foreign Affairs, Foreign Affairs, 18 Aug. 2026
  • With the correct number of dots, no arrangement, however cunning, can dodge these shapes forever.
    — Jack Murtagh, Scientific American, 10 Aug. 2026
Definition of cunning
Adjective
  • Violations of the law are a deceptive trade practice, which can be investigated by the state attorney general's office.
    — Seth Klamann, Denver Post, 12 Aug. 2026
  • Protection of the president has often required deft and deceptive tactics by the Secret Service.
    — Donald J. Mihalek, ABC News, 11 Aug. 2026
Definition of deceptive
Adjective
  • After Culkin penned a sweet message to Song on Instagram at the time, the actress responded by posting a cute Polaroid-style snap of the couple sharing a kiss on her own Instagram page.
    — Natalia Senanayake, PEOPLE, 14 Aug. 2026
  • There are some really cute rooftop spots in the Beverly Hills area.
    — Kailyn Brown, Los Angeles Times, 14 Aug. 2026
Definition of cute
Adjective
  • The fraudulent registration charge is a misdemeanor; the other two are felonies, involving activity during September 2024 and October 2025, pending in the 39th District Court in Macomb County.
    — Paula Wethington, CBS News, 13 Aug. 2026
  • Two insurance companies affiliated with Walters happen to be under federal investigation for potential fraudulent loans, according to the Los Angeles Times.
    — Theresa Braine, New York Daily News, 12 Aug. 2026
Definition of fraudulent
Adjective
  • There’s the slick, glad-handing publisher of Hamptons magazine, and the feisty Citarella market scion who would love to have her picture featured in its pages.
    — Naomi Fry, New Yorker, 15 Aug. 2026
  • When shoppers lose their traction on slick, unforgiving floors, severe bruising, fractured wrists, spinal pain, and concussions are common results.
    — Miami Herald, Miami Herald, 14 Aug. 2026
Definition of slick
Adjective
  • For shady slopes, this evergreen, herbaceous perennial with striking yellow blooms makes excellent groundcover under trees.
    — Mary Marlowe Leverette, Southern Living, 11 Aug. 2026
  • The massive trees had long been a home for rare species and a shady place for neighbors to gather.
    — Trevor Hughes, USA Today, 11 Aug. 2026
Definition of shady
Adjective
  • Her lyrics, like those of many of her biggest musical influences, are dense texts, full of winking allusions and subtle references to records, bands, and albums that have shaped her own songwriting.
    — Jonathan Bernstein, Rolling Stone, 14 Aug. 2026
  • Izquierdo recommends asking for softly disconnected layers, a blended curtain fringe, and soft, subtle texture.
    — Loren Savini, Allure, 14 Aug. 2026
Definition of subtle
Adjective
  • The rule also failed to tackle all of the ways trusts and other vehicles provide impenetrable secrecy for the wealthy and the crooked alike.
    — Casey Michel, The Atlantic, 14 Aug. 2026
  • In Salinger’s narrative, Pencey is plagued by a population of troubled youth, crooked teachers, and spoiled rich kids, a mixture that often begat abuse.
    — Literary Hub, Literary Hub, 10 Aug. 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 19 Aug. 2026.

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