1
as in difficult
requiring considerable physical or mental effort
an exceptionally challenging brainteaser
Synonyms & Similar Words
Relevance
Antonyms & Near Antonyms
2
as in demanding
requiring much time, effort, or careful attention
a challenging test designed to whittle down the number of contestants
Synonyms & Similar Words
Antonyms & Near Antonyms
1
as in questioning
to demand proof of the truth or rightness of
don't hesitate to challenge any statement that generalizes about people
Synonyms & Similar Words
Antonyms & Near Antonyms
2
3
as in requiring
to have as a requirement
having to put up with an overbearing boss challenges forbearance
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Antonyms & Near Antonyms
Example Sentences
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Recent Examples of challenging
ArsTechnica, 10 June 2026
That’s a little challenging right now, to put it mildly.
—Derek Lawrence, Entertainment Weekly, 10 June 2026
E.r. Pulgar, Pitchfork, 11 June 2026
Advertisement Still, Trump’s apparent glibness comes as the Republican Party faces what could be challenging midterm elections, as the economy and affordability remain top concerns for voters.
—Chad De Guzman, Time, 11 June 2026
See All Example Sentences for challenging
Adjective
The animation above shows how DiffusionGemma was tuned to solve Sudoku puzzles, which is a notoriously challenging task for standard autoregressive AI models because each token depends on future tokens.
—ArsTechnica, 10 June 2026
That’s a little challenging right now, to put it mildly.
—Derek Lawrence, Entertainment Weekly, 10 June 2026
Verb
Her political outspokenness and fearlessness in challenging the danger women face in flaunting their sexuality, particularly in her native Argentina, is one of her strengths, as is her ability to imagine a new world where that violence doesn’t exist.
—E.r. Pulgar, Pitchfork, 11 June 2026
Advertisement Still, Trump’s apparent glibness comes as the Republican Party faces what could be challenging midterm elections, as the economy and affordability remain top concerns for voters.
—Chad De Guzman, Time, 11 June 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
-
The verdict was delivered amid difficult personal circumstances for Mette-Marit, Hoiby’s mother, who needs a lung transplant for pulmonary fibrosis.—
Reuters,
CNN Money,
15 June 2026
-
Otherwise, those prospects start becoming large contracts that stand more difficult to move or aggregate.—
Ira Winderman,
Sun Sentinel,
14 June 2026
Adjective
-
The formula is more demanding than most people realize, and the research behind it suggests close friendships may matter more for long-term health than almost anything else.—
Hanna Wickes,
Fort Worth Star-Telegram,
16 June 2026
-
Why do humanoids still struggle The problem is that battlefields are among the most demanding environments imaginable.—
Kaif Shaikh,
Interesting Engineering,
16 June 2026
Verb
-
According to the affidavit, investigators confronted Holmes with the surveillance video and witness statements during questioning.—
Marvin Hurst,
CBS News,
16 June 2026
-
As Fujimori’s lead slowly widened in the past few days, Sánchez intensified his efforts to rally supporters, questioning the integrity of the vote review process and framing the dispute as a broader fight for democratic legitimacy.—
Antonio María Delgado,
Miami Herald,
16 June 2026
Verb
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The site is said to be the only location with the capacity to replace the 40 military aircraft Kyiv said were damaged or destroyed in June's daring Operation Spiderweb drone attacks that targeted planes which can launch cruise missiles.—
Brendan Cole,
MSNBC Newsweek,
3 July 2025
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On the broadcast, the announcers explained that Freddie Freeman, Max Muncy, and Kiké Hernández stood in front of Roberts, glaring at him, daring him to remove their friend, their comrade, their beloved teammate from the game.—
Dan Freedman,
Forbes.com,
3 July 2025
Verb
-
The pair say their grief journeys are not linear, requiring effort every day — sometimes just to get out of bed.—
Caroline Cummings,
CBS News,
14 June 2026
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In 2010, the judge granted a permanent injunction, requiring, among other things, that the farm stop selling raw milk beyond California and take down any statements promoting its health benefits.—
CNN Money,
CNN Money,
14 June 2026
Adjective
-
With the when, where and who will play whom at the 2026 World Cup all locked in, how do the groups rank from the easiest to the toughest?—
Andrew Greif,
NBC news,
12 June 2026
-
Opening a restaurant in downtown Boise is a tough racket.—
Michael Deeds,
Idaho Statesman,
11 June 2026
Verb
-
Pratt has yet to put out a statement conceding the race or contesting the results.—
National Correspondent,
Los Angeles Times,
11 June 2026
-
Towns picked up his first foul 18 seconds into the game while contesting Fox at the rim.—
C.J. Holmes,
New York Daily News,
11 June 2026
Verb
-
Future legislative assemblies would be able to raise taxes without needing voter approval, so long as it is offset by decreasing the income tax.—
Jack Harvel,
Kansas City Star,
15 June 2026
-
For anyone needing to catch up on past episodes, Paramount+ is the main hub for that.—
Brayden Garcia,
Fort Worth Star-Telegram,
15 June 2026
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 18 Jun. 2026.
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