1
as in difficult
requiring considerable physical or mental effort
an exceptionally challenging brainteaser
Synonyms & Similar Words
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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
-
JSerra navigated a difficult regular-season schedule, then avoided upsets in the playoffs.—
Eric Sondheimer,
Los Angeles Times,
8 June 2026
-
But the strength of his acidic, strong, difficult performance was too powerful for the Tonys to deny.—
Rebecca Alter,
Vulture,
8 June 2026
Adjective
-
Autonomy can absorb repetitive, lower-value, or cognitively demanding tasks so crews can focus on judgment, decision-making, and mission execution – the things humans still do best.—
Tim Burns,
Fortune,
9 June 2026
-
The fuchsia tone is, of course, the most attention-demanding, and black is always a safe bet—especially for more formal events.—
Alexandra Malmed,
InStyle,
9 June 2026
Verb
-
Under prosecutors’ questioning, the witness agreed that his previous belief that Anthony was surrounded when the stabbing happened was incorrect.—
Suzanne Gamboa,
NBC news,
8 June 2026
-
After questioning witnesses, detectives determined Williams had gotten into a domestic dispute with another person who was with Taylor, and Williams pulled out a semiautomatic rifle and fired multiple shots, shooting Taylor in the back.—
Todd Feurer,
CBS News,
8 June 2026
Verb
-
State workers from six departments were bestowed with California’s highest honor for public employees who have performed daring rescues in extreme conditions, including floods, wildfires and active shooter incidents.—
William Melhado,
Sacbee.com,
13 June 2026
-
Wang has made a habit of wearing daring looks at recent events.—
Meg Walters,
InStyle,
13 June 2026
Verb
-
To become a licensed drone pilot within the department, officers must apply, interview, and pass an FAA exam — requiring knowledge of nautical and weather chart reading.—
Walker Armstrong,
San Diego Union-Tribune,
7 June 2026
-
California and other states enacted similar laws in 2023 requiring heavy metal testing and disclosure for baby food, but, at that time, formula was not included.—
Rachel Fobar,
Daily News,
7 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
-
More than $60 million and tens of thousands of hours of labor have been poured into building the arena, according to a court filing from the National Park Service, which oversees the South Lawn and is contesting a lawsuit meant to block the event.—
ABC News,
ABC News,
11 June 2026
-
Pratt has yet to put out a statement conceding the race or contesting the results.—
National Correspondent,
Los Angeles Times,
11 June 2026
Verb
-
Both of those teams won championships, the Bulls needing six games to oust the Phoenix Suns, the Rockets going home after winning those first two games in Orlando and sweeping the Magic.—
CBS News,
CBS News,
6 June 2026
-
Others watch their kids go from needing a pair of shin guards to hauling around an entire bag of equipment just to play soccer.—
New Atlas,
New Atlas,
6 June 2026
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 15 Jun. 2026.
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