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

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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

The Idaho Consumer Protection Act, enacted in 1971, protects consumers from false, deceptive or misleading representations, advertising, pricing and contracts.

— Harllie Stevenson, Idaho Statesman, 14 Oct. 2026
What Apple says about suspicious iMessages Apple says this type of deceptive messaging uses social engineering, a tactic in which scammers rely on impersonation and manipulation to persuade people to share personal information.

— Kurt Knutsson, FOXNews.com, 13 Oct. 2026

Definition of deceptive

Adjective

Philadelphia police are also working with GoFundMe to prevent fraudulent fundraisers, the department said in a post on Facebook.

— Laura Fay, CBS News, 15 Oct. 2026
Dispute fraudulent charges and accounts, follow up on your identity theft report and request that fraudulent information be removed from your credit reports.

— Kurt Knutsson, FOXNews.com, 15 Oct. 2026

Definition of fraudulent

Adjective

Jack Hughes scored on a breakaway off a slick pass from Jesper Bratt early in overtime, lifting the New Jersey Devils to a 5-4 win over the Detroit Red Wings on Tuesday night.

— CBS News, CBS News, 14 Oct. 2026
The next email had a slick poster promoting the Zoom event, with the book cover as the backdrop and blurbs from the Economist and other publications.

— Snigdha Poonam, The Dial, 13 Oct. 2026

Definition of slick

Adjective

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
If weather permits, be sure to dine at Oliveto Restaurant & Lounge Bar, which sits beneath a shady grove of trees and overlooks the pool and vineyard.

— Condé Nast, Condé Nast Traveler, 13 Oct. 2026

Definition of shady

Adjective

Coleman said each design has its own distinct character and can be styled individually, either as a subtle everyday detail or a sculptural statement.

— Tianwei Zhang, Footwear News, 15 Oct. 2026
As the researchers saw, introducing random mutation could still make subtle structural tweaks that produced enzymes that were considerably more active.

— ArsTechnica, ArsTechnica, 14 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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“Guileful.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/guileful. Accessed 21 Oct. 2026.

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Synonyms of guileful

adjective

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