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

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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

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

Meta will be subject to an injunction prohibiting it from making further false, misleading, or deceptive statements around its safety features.

— Jill Goldsmith, Deadline, 26 Aug. 2026
The agency has said deceptive or unfair data practices can violate existing consumer protection laws.

— Kurt Knutsson, FOXNews.com, 24 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

Tashia McKenzie, 36, faces one count each of fraudulent claim or receipt of benefits and second-degree larceny, the Connecticut Division of Criminal Justice said in a news release Tuesday.

— Justin Muszynski, Hartford Courant, 25 Aug. 2026
Verification can be particularly important because fraudulent job listings have become a concern for applicants and job platforms alike.

— Angelica Leicht, CBS News, 24 Aug. 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

Greenspan was renowned for his formidable data-crunching capabilities, sharp reading of market psychology, and subtle, often elusive communication style.

— , CNBC, 28 Aug. 2026
The cabin interiors are built from a lovely blonde wood, which was aesthetically pleasing, if a little creaky at times, while the white linens on the comfortable queen bed were a subtle reminder that this is a luxury accommodation.

— Condé Nast, Condé Nast Traveler, 28 Aug. 2026

Definition of subtle

Adjective

Cowin soon shifted to straighter technical methods applied to crooked storylines.

— Leah Ollman, Los Angeles Times, 25 Aug. 2026
In addition, there are crooked cops on the inside trying to spring El Chapo, so the arresting officers need to quickly figure out who to trust.

— K. Thor Jensen, PC Magazine, 21 Aug. 2026

Definition of crooked

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guile

guileful

guilefulness

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“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 2 Sep. 2026.

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Synonyms of guileful

adjective

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