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
Sam Crenshaw, CBS News, 8 Apr. 2026
Campbell said the deal requires aligning multiple players in a challenging lending environment.
—John Magsam, Arkansas Online, 8 Apr. 2026
Carmela Karcher, CBS News, 9 Apr. 2026
Redick said both players were medically cleared and both insisted on challenging the league-leading Thunder in the second half.
—Los Angeles Times, 9 Apr. 2026
See All Example Sentences for challenging
Adjective
Will the new facilities and challenging conditions shape a memorable outcome?
—Sam Crenshaw, CBS News, 8 Apr. 2026
Campbell said the deal requires aligning multiple players in a challenging lending environment.
—John Magsam, Arkansas Online, 8 Apr. 2026
Verb
There's no way they're supposed to be challenging traffic on main drags in town.
—Carmela Karcher, CBS News, 9 Apr. 2026
Redick said both players were medically cleared and both insisted on challenging the league-leading Thunder in the second half.
—Los Angeles Times, 9 Apr. 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
-
Such claims of penury, however, were difficult to square with certain facts.—
Patrick Radden Keefe,
New Yorker,
13 Apr. 2026
-
Over time, my relationship with my wife has become very difficult.—
R. Eric Thomas,
Chicago Tribune,
12 Apr. 2026
Adjective
-
The hours were long, stressful, and emotionally demanding.—
Richard Brody,
New Yorker,
6 Apr. 2026
-
Wheeler coach Larry Thompson saw Landrew’s basketball IQ and physical toughness lead his team through some of its most demanding moments.—
Jack Leo,
AJC.com,
6 Apr. 2026
Verb
-
The individual is awaiting questioning by Ontario Police Department detectives who are en route.—
Michael Dorgan,
FOXNews.com,
7 Apr. 2026
-
The Microsoft co-founder is scheduled for questioning on June 10, the source said.—
Graham Kates,
CBS News,
7 Apr. 2026
Verb
-
Elsewhere on the menu, coconut and tamarind flavors mingle, producing fusion-style flavors that push dishes just to the edge, enough to be daring but not too much to alienate diners.—
Michael James Rocha,
San Diego Union-Tribune,
10 Apr. 2026
-
His own series of daring explorations.—
Courtney Crowder,
USA Today,
10 Apr. 2026
Verb
-
Bollinger's amendments included requiring the authority to receive Quorum Court approval by resolution before exercising eminent domain in Benton County.—
Arkansas Online,
Arkansas Online,
12 Apr. 2026
-
This, and the hospital’s security, had been a point of contention in recent years after a number of assaults on staff and forensic patients (usually kept there through the courts) escaping the hospital grounds, requiring a police response.—
Peter Currier,
Boston Herald,
12 Apr. 2026
Adjective
-
As the inspirational Moon glides into your 7th House of Allies, your expressive nature invites connection, and your generous spirit lightens tough conversations.—
Tarot.com,
Baltimore Sun,
10 Apr. 2026
-
One factor is that the Highlanders, a Division 3 team, haven’t faced the toughest schedule.—
Don Norcross,
San Diego Union-Tribune,
9 Apr. 2026
Verb
-
From there, you’re introduced to your guide for your adventures in Japan, meet your starter cars (those would be an ST205 Toyota Celica GT-Four, widebody S13 Nissan Silvia, and—wait for it—a K5 GMC Jimmy), and can immediately begin contesting races to qualify for the big show, the Horizon Festival.—
Adam Ismail,
The Drive,
8 Apr. 2026
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There are at least three more pending investigations that are still outstanding, according to OSHA’s website, and Boring Company is currently contesting eight citations it was issued regarding chemical burns in 2024.—
Jessica Mathews,
Fortune,
24 Mar. 2026
Verb
-
Miami won the season series 3-1, resulting in Charlotte needing to finish one game ahead of the Heat to avoid having to win two outings on the road to reach the actual playoff field for the first time in a decade.—
Roderick Boone,
Charlotte Observer,
13 Apr. 2026
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We’re spread too thin, needing to connect complex infrastructures of storytelling instead of engaging in-depth with a single tale.—
Matthew Razak,
Space.com,
13 Apr. 2026
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 14 Apr. 2026.
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