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
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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
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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
Jim Hemphill, IndieWire, 4 Mar. 2026
Our crews worked around the clock in challenging conditions to clear snow, repair damage and safely restore service.
—Jesse Zanger, CBS News, 4 Mar. 2026
Jamie Carter, Space.com, 26 Feb. 2026
Runway lengths, locations, and operational characteristics referenced in this article are drawn from analysis compiled by Bristol Groundschool, a pilot-training organisation that documents technically challenging airstrips used in real-world aviation training and operations.
—Karina Acharya, Condé Nast Traveler, 26 Feb. 2026
See All Example Sentences for challenging
Adjective
Surprisingly, Evelyn found some of the show’s more subtle costumes to be the most challenging, as in the case of the FBI agents on Forst’s trail.
—Jim Hemphill, IndieWire, 4 Mar. 2026
Our crews worked around the clock in challenging conditions to clear snow, repair damage and safely restore service.
—Jesse Zanger, CBS News, 4 Mar. 2026
Verb
Add the fact that the sky will be fairly bright in the west around the sunset point, and imaging this event will be challenging.
—Jamie Carter, Space.com, 26 Feb. 2026
Runway lengths, locations, and operational characteristics referenced in this article are drawn from analysis compiled by Bristol Groundschool, a pilot-training organisation that documents technically challenging airstrips used in real-world aviation training and operations.
—Karina Acharya, Condé Nast Traveler, 26 Feb. 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
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Mascherano said his second-half lineup change was a difficult one to make.—
Miami Herald,
Miami Herald,
2 Mar. 2026
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The winners said the warmer-than-normal conditions made a challenging course even more difficult.—
Bo Evans,
CBS News,
1 Mar. 2026
Adjective
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The base model starts at $1,599, while the higher-end Studio Display XDR starts at $3,299 and adds features aimed at more demanding professional use cases, including higher brightness, mini-LED backlighting and a faster refresh rate.—
MacKenzie Sigalos,
CNBC,
3 Mar. 2026
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Or in the dancer Mira Nadon, whose body contains a natural shadow, revealing a tension between musical dissonance and the relentlessly demanding and athletic steps she is pushed to perform.—
Jennifer Homans,
New Yorker,
2 Mar. 2026
Verb
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The closed-door depositions showed how Republican lawmakers at times seemed not able to resist the spectacle of questioning a couple who for decades led the Democratic Party.—
Stephen Groves,
Fortune,
3 Mar. 2026
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Neighbors in Baltimore County are questioning the use of deadly force after a man, allegedly experiencing a mental health crisis, was found dead following police gunfire at his home Wednesday.—
Tara Lynch,
CBS News,
3 Mar. 2026
Verb
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Burke helped lead Fire Country as Vince Leone, the tough-as-nails battalion chief running Station 42 and calling the shots as his team battled wildfires and pulled off daring rescues.—
Allison DeGrushe,
Entertainment Weekly,
27 Feb. 2026
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Earlier this month, Censori, who is debuting an art installation in Seoul, spoke to Vanity Fair about her penchant for daring looks.—
Meg Walters,
InStyle,
27 Feb. 2026
Verb
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Drew Angerer / Getty Images file For months, school officials have floated proposals to relocate or close at least four middle schools on the Upper West Side, citing low enrollment, funding squeezes, academic performance and compliance with a 2022 law requiring class-size reductions by 2028.—
Matt Lavietes,
NBC news,
1 Mar. 2026
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That means requiring sufficient space be left for pedestrians, including people with mobility limitations, and for bikes.—
Michael Pollack,
New York Daily News,
1 Mar. 2026
Adjective
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The Heat’s climb to get out of the play-in tournament this season just got tougher.—
Anthony Chiang,
Miami Herald,
27 Feb. 2026
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Regulation overseas may be a tougher sell.—
David Goldman,
CNN Money,
27 Feb. 2026
Verb
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Performing Under Pressure in Milan At the 2026 Games, Gu is the lone female freeskier contesting all three freestyle events.—
Hanna Wickes,
Miami Herald,
19 Feb. 2026
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Paxton’s office is contesting the boundaries of the district and wants the land tied to The Meadow development removed.—
Nick Wooten,
Dallas Morning News,
16 Feb. 2026
Verb
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So far, DeSantis’ administration has spent at least $573 million for immigration efforts over the past three years, including at the Everglades facility — without needing approval by state lawmakers, thanks to the Emergency Preparedness and Response Fund created by the Legislature in 2022.—
Kate Payne,
Sun Sentinel,
1 Mar. 2026
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The number of people needing vouchers spawned another problem.—
Timia Cobb
Breaking News Reporter,
Dallas Morning News,
1 Mar. 2026
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 6 Mar. 2026.
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