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
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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
Jessica Puckett, Condé Nast Traveler, 11 Feb. 2026
Purchasing through Troop 2026 is one way people can support Girl Scouts during this challenging season, Freese said.
—Talia McWright, Twin Cities, 11 Feb. 2026
Magi Helena, Dallas Morning News, 5 Feb. 2026
These conditions can make driving challenging, so exercise extreme caution on the road, and if possible, consider delaying your trip.
—Southern California Weather Report, Oc Register, 29 Jan. 2026
See All Example Sentences for challenging
Adjective
In an excerpt from her new book, Feral, writer Emily Pennington traverses the challenging terrain of Alaska's Gates of the Arctic—part of a years-long journey to visit every national park in the United States.
—Jessica Puckett, Condé Nast Traveler, 11 Feb. 2026
Purchasing through Troop 2026 is one way people can support Girl Scouts during this challenging season, Freese said.
—Talia McWright, Twin Cities, 11 Feb. 2026
Verb
While there are good energies available to assist you, there are also challenging energies that could function as tests or lessons.
—Magi Helena, Dallas Morning News, 5 Feb. 2026
These conditions can make driving challenging, so exercise extreme caution on the road, and if possible, consider delaying your trip.
—Southern California Weather Report, Oc Register, 29 Jan. 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
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Training and case management through FRAP is supposed to help attorneys deal with what Clegg calls a difficult area of law.—
Raynee Howell,
Oklahoma Watch,
9 Feb. 2026
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Will this race and the other changes create an opportunity for NASCAR to turn the page on its difficult 2025?—
Jeff Gluck,
New York Times,
9 Feb. 2026
Adjective
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The truth is, managing a game and operating within a system of offense are two of the most important things about excelling at the most demanding position in professional sports.—
Jerry McDonald,
Mercury News,
10 Feb. 2026
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Turns out, von Allmen had the better inside track on the demanding hill.—
Pat Graham,
Baltimore Sun,
7 Feb. 2026
Verb
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Late Tuesday evening, hours after the images were released, the Pima County Sheriff’s Department and the FBI detained a person for questioning in the case.—
Dakin Andone,
CNN Money,
11 Feb. 2026
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Tensions flared and the hearing sparked heated exchanges — the Democrats comparing the enforcement operations to Nazi Germany and questioning how the administration officials will be judged — the chairman at times gaveling the lawmakers back to order.—
Rebecca Santana,
Chicago Tribune,
10 Feb. 2026
Verb
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But in their daring escape through the window, the crown of Empress Eugénie slipped from their grasp and was left battered on the pavement below.—
Laura Sharman,
CNN Money,
6 Feb. 2026
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Florida Highway Patrol, which is deputized to do immigration enforcement, conducting an arrest while refusing to say why, violently arresting a family member for daring to ask why the arrest is happening, and threatening to arrest a bystander in a public street who is filming.—
Shira Moolten,
Sun Sentinel,
6 Feb. 2026
Verb
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In their request for a rehearing, the nonprofits said their members and communities were unfairly being forced to pay to keep a costly and unreliable plant operating and that the department didn't even comply with the law requiring it to show why this was the best alternative.—
MATTHEW DALY,
Arkansas Online,
8 Feb. 2026
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Delays and mistreatment reported Over the first four days of the crossing’s opening, just 36 Palestinians requiring medical care were allowed to leave for Egypt, plus 62 companions, according to United Nations data.—
Samy Magdy,
Los Angeles Times,
8 Feb. 2026
Adjective
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Most importantly, Alvarado relishes in his role as a tough-nosed, point-of-attack defender, an area the Knicks have had trouble despite building a roster with notable defenders across all positions.—
Kristian Winfield,
New York Daily News,
5 Feb. 2026
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With a durable and tough rubber sole featuring Vibram's TC5+ technology, each step offers the right amount of flex and resistance for a comfortable hiking experience.—
Michael Cappetta,
Travel + Leisure,
5 Feb. 2026
Verb
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Christian Braun helped extend the game to OT by defending Brunson and contesting his step-back attempt to win it on the ensuing possession.—
Bennett Durando,
Denver Post,
5 Feb. 2026
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While 5,400 drivers fighting their school-bus violations failed to get news of their legal wins, others could see their fines voided without even contesting their tickets, according to the audit.—
Douglas Hanks,
Miami Herald,
4 Feb. 2026
Verb
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Without needing to improve, Mathilde Gremaud takes a victory lap down the slope wearing the Swiss flag like a cape around her neck.—
Isabel Yip,
NBC news,
9 Feb. 2026
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There’s wanting and liking—and then there’s needing.—
Dhruv Khullar,
New Yorker,
9 Feb. 2026
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 13 Feb. 2026.
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