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

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

But several Theranos staffers and journalists say Holmes was frequently deceptive and would lie repeatedly, especially when confronted with facts.

— Los Angeles Times, Los Angeles Times, 21 Oct. 2026
California and Hawaii, for example, are two states that have banned sharing deceptive AI content about candidates in the months around an election.

— Jordi Calvet-Bademunt, The Conversation, 20 Oct. 2026

Definition of deceptive

Adjective

At their on-screen meet cute, Apatow hands Bamford $500 cash just to pitch her on her own documentary.

— Tony Maglio, HollywoodReporter, 23 Oct. 2026
The showstopper is a very cute idea where each baker has to make a dessert cart with at least three classic desserts on it.

— Brian Moylan, Vulture, 23 Oct. 2026

Definition of cute

Adjective

Federal authorities said her husband and several other individuals stole millions of dollars from the casino by creating fraudulent credit vouchers.

— Sergio Candido, CBS News, 22 Oct. 2026
Malek also faces charges for allegedly submitting fraudulent Paycheck Protection Program (PPP) loan applications in 2021.

— Louis Casiano, FOXNews.com, 22 Oct. 2026

Definition of fraudulent

Adjective

Walid Itayim plays a free and funky guitar solo over Sami Shabshab’s slick bassline, but the lyrics pierce straight through the upbeat tune.

— Shy Clara Thompson, Pitchfork, 23 Oct. 2026
And belief isn’t manufactured by marketing departments, slick hype videos or breathless preseason predictions.

— Mike Bianchi, The Orlando Sentinel, 22 Oct. 2026

Definition of slick

Adjective

Many shady electronics companies are happy to sell you the wrong component for the wrong price.

— Tim Stevens, ArsTechnica, 19 Oct. 2026
The fake image was attention-grabbing, shady, and timely — in other words, perfect for social media virality but a potential liability for the parties involved.

— Mia Sato, The Verge, 15 Oct. 2026

Definition of shady

Adjective

The rash can be more subtle on darker skin tones, but a bumpy or textured feel is often present.

— Sara Tenenbaum, CBS News, 21 Oct. 2026
The last major change was the iPhone X, which dropped the home button almost a decade ago, and even that was a fairly subtle improvement.

— Nilay Patel, The Verge, 21 Oct. 2026

Definition of subtle

Adjective

Finding no legal recourse in a city with a crooked police department and judiciary, Matt gives in to despair.

— Frank Scheck, HollywoodReporter, 21 Oct. 2026
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

Definition of crooked

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guileful

guilefulness

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Style

“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 29 Oct. 2026.

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Synonyms of guileful

adjective

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