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

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

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
  • Supporters of the administration view this back and forth as a cunning ploy to buy time for the United States to position itself more advantageously for a confrontation.
    — Leonard A. Schuette, Foreign Affairs, 25 Aug. 2026
  • Owen is bamboozled by a cunning opportunist, handcuffed, and robbed in his underwear.
    — Alexandra Schwartz, New Yorker, 21 Aug. 2026
Definition of cunning
Adjective
  • The technology was also tested against deceptive behaviour, an in a different scenario, fishing boats appeared to retreat while vessels from another direction accelerated toward the coastguard ship.
    — Bojan Stojkovski, Interesting Engineering, 30 Aug. 2026
  • The siblings are likely to dispute Jeanie’s characterization of their actions as deceptive and clandestine, perhaps by pointing to communications with their sister and her responses.
    — Michael McCann, Sportico.com, 28 Aug. 2026
Definition of deceptive
Adjective
  • But don’t let the cute style fool you—this look is super practical, too.
    — Kayla Becker, Travel + Leisure, 29 Aug. 2026
  • Continue down Main Street in Catskill to find tons of the cute shops upstate New York is known for, in particular Stay Forever for gifts, Spike’s for records, and Magpie for used books.
    — Condé Nast, Condé Nast Traveler, 28 Aug. 2026
Definition of cute
Adjective
  • Police said Pabst later learned that the pickup documents were fraudulent.
    — Saleen Martin, USA Today, 3 Sep. 2026
  • Washington rejected the legitimacy of the 2018 election that returned Maduro to office and also considered his 2024 reelection fraudulent.
    — Antonio María Delgado, Miami Herald, 3 Sep. 2026
Definition of fraudulent
Adjective
  • Paranormal Activity, the play, builds to the sort of slick and grisly finale that would be just right for the end of a cruel horror movie, but that lands awkwardly onstage.
    — Jackson McHenry, Vulture, 26 Aug. 2026
  • The government’s YouTube series featuring the transportation secretary is slick, well-made and about the Duffys, not the nation.
    — Monica Hesse, Washington Post, 25 Aug. 2026
Definition of slick
Adjective
  • But for now, CyberLeek is trying to monetize the GTA 6 leaks by asking for shady donations.
    — Michael Kan, PC Magazine, 25 Aug. 2026
  • Others sat in shady spots on Montrose Avenue where the parade units combined with waiting community groups to end the parade at the festival grounds.
    — Karie Angell Luc, Chicago Tribune, 24 Aug. 2026
Definition of shady
Adjective
  • That possibility, however subtle, may have helped drive the legal chaos that unfolded in Baton Rouge just 48 hours before LSU was scheduled to take the field.
    — Trey Wallace OutKick, FOXNews.com, 4 Sep. 2026
  • Birdseye maple recurs as a detail on furniture and banisters, along with subtle copper details and velvet seating.
    — Miles Socha, Footwear News, 3 Sep. 2026
Definition of subtle
Adjective
  • The workers would be fined if their tails were dirty, their satin ears crooked.
    — Jennifer Hassan, USA Today, 3 Sep. 2026
  • Kennedy’s Albany is a vital, violent place, a hothouse of gangsters, pool hustlers, bums, crooked politicians, and showgirls.
    — Cynthia Zarin, Harpers Magazine, 1 Sep. 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 6 Sep. 2026.

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