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
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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
Jules-Pierre Malartre, Space.com, 17 June 2026
Students would write responses to challenging literature—from Michelle Alexander to Mark Twain—connecting the works to their own lives and broader social issues, and then work together to critique each other’s writing.
—Literary Hub, 17 June 2026
Emily Price, Forbes.com, 18 June 2026
Someone could be mirroring your intensity or challenging your confidence.
—Valerie Mesa, PEOPLE, 17 June 2026
See All Example Sentences for challenging
Adjective
The moon passes directly in front of Venus during a rare daylight occultation on June 17, 2026, creating one of the month's most unusual and technically challenging skywatching events.
—Jules-Pierre Malartre, Space.com, 17 June 2026
Students would write responses to challenging literature—from Michelle Alexander to Mark Twain—connecting the works to their own lives and broader social issues, and then work together to critique each other’s writing.
—Literary Hub, 17 June 2026
Verb
The site is challenging to farm and even more challenging to harvest.
—Emily Price, Forbes.com, 18 June 2026
Someone could be mirroring your intensity or challenging your confidence.
—Valerie Mesa, PEOPLE, 17 June 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
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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
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Otherwise, those prospects start becoming large contracts that stand more difficult to move or aggregate.—
Ira Winderman,
Sun Sentinel,
14 June 2026
Adjective
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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
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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
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According to the affidavit, investigators confronted Holmes with the surveillance video and witness statements during questioning.—
Marvin Hurst,
CBS News,
16 June 2026
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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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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
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Wang has made a habit of wearing daring looks at recent events.—
Meg Walters,
InStyle,
13 June 2026
Verb
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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
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McIlroy bogeyed 18 to finish at one under, squarely in the hunt, considering the tough conditions limited scoring.—
Ian Miller OutKick,
FOXNews.com,
19 June 2026
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Parker, a former Eagles assistant, has risen quickly through the NFL coaching ranks and now faces a tough task with a roster full of new faces and high expectations.—
Briana Aldridge,
CBS News,
18 June 2026
Verb
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Elimination of those missiles was one of the primary aims of the war, and thousands of Iranians, as well as more than a dozen Americans, died contesting it.—
Graeme Wood,
The Atlantic,
18 June 2026
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During jury selection on Monday, lawyers disclosed that Brown had accepted partial responsibility in the case after contesting the claims for years.—
Nancy Dillon,
Rolling Stone,
16 June 2026
Verb
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Since August 2024, six Americans were hospitalized with injuries due to jet ski accidents, with three needing emergency medical evacuations to the United States, according to the security alert.—
Kathleen Wong,
USA Today,
16 June 2026
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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
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 21 Jun. 2026.
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