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
Georgina Jedikovska, Interesting Engineering, 29 Apr. 2026
Facing the next challenge A challenging district schedule featuring 2025 Class 5A Division I state champion Aledo, a strong Granbury squad, and a flurry of competitive teams has helped prepare Brewer for the postseason.
—Charles Baggarly, Fort Worth Star-Telegram, 28 Apr. 2026
Sharon Bernstein, Sacbee.com, 30 Apr. 2026
For Oakley, being a drag king is about challenging masculinity rather than impersonating someone, which is what older male impersonators have traditionally done.
—Nicole MacIas Garibay, Los Angeles Times, 30 Apr. 2026
See All Example Sentences for challenging
Adjective
However, integrating this into a soft, curved device is particularly challenging.
—Georgina Jedikovska, Interesting Engineering, 29 Apr. 2026
Facing the next challenge A challenging district schedule featuring 2025 Class 5A Division I state champion Aledo, a strong Granbury squad, and a flurry of competitive teams has helped prepare Brewer for the postseason.
—Charles Baggarly, Fort Worth Star-Telegram, 28 Apr. 2026
Verb
In Placer County, Rocklin Mayor Dave Bass is challenging an incumbent judge, Leon Dixson.
—Sharon Bernstein, Sacbee.com, 30 Apr. 2026
For Oakley, being a drag king is about challenging masculinity rather than impersonating someone, which is what older male impersonators have traditionally done.
—Nicole MacIas Garibay, Los Angeles Times, 30 Apr. 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
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But with the Lightning taking back home-ice advantage with this win and the series shifting back to Tampa, where Cooper will have full control of the matchup, the task becomes that much more difficult for the Suzuki line.—
Arpon Basu,
New York Times,
27 Apr. 2026
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Tornadoes are extremely difficult to see and confirm at night.—
STAR-TELEGRAM WEATHER BOT,
Fort Worth Star-Telegram,
26 Apr. 2026
Adjective
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Reliable Service as an Operational Standard Clients in Dallas-Fort Worth should expect something more demanding than friendliness and something less theatrical than branding.—
Connie Etemadi,
USA Today,
27 Apr. 2026
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The dual-motor setup targets higher output and improved traction for more demanding driving conditions.—
Bojan Stojkovski,
Interesting Engineering,
25 Apr. 2026
Verb
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The aggressive political gains DeSantis and Republicans seek also have some in the party questioning whether the new map would put GOP incumbents at risk of losing future elections.—
Elizabeth Robinson,
NBC news,
28 Apr. 2026
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Despite the apology, Camp Mystic’s plans to reopen in late May with nearly 900 girls have angered victims’ families, and state officials are questioning whether the license should be renewed.—
Jim Vertuno,
Los Angeles Times,
28 Apr. 2026
Verb
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There’s a reason the mayor is all but daring his social media followers to complain about this site.—
Sam McDowell,
Kansas City Star,
23 Apr. 2026
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Jasmin Reese approaches interiors with an artist’s eye, embracing daring color combinations and unexpected accents in her impactful rooms.—
Dan Howarth,
Architectural Digest,
19 Apr. 2026
Verb
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The State Tax Commission issued an order in May 2025 requiring the county to cap any property value increases in the 2025 assessment cycle at 15%.—
Kansas City Star,
Kansas City Star,
26 Apr. 2026
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Paschal said this bill takes a different approach than requiring hard verification from users or relying on social media companies to analyze users’ behavior to estimate their ages.—
Nick Coltrain,
Denver Post,
26 Apr. 2026
Adjective
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Lightly coated with oil and tossed occasionally in a searing hot skillet or wok, even tough beans turn silky, and ready to coat in a finishing blast of chiles.—
The Bon Appétit Staff,
Bon Appetit Magazine,
1 May 2026
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Comfortable travel can be achieved with stretchy, breathable pants, but securing a pair that hits those marks while looking stylish can be tough.—
Rachel Trujillo,
Travel + Leisure,
30 Apr. 2026
Verb
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So your rotations aren’t just about contesting 3s.—
Bennett Durando,
Denver Post,
30 Apr. 2026
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Under Mayor Bill de Blasio, the city initiated a policy of rarely contesting such claims, meaning that, in most cases, all a family had to do to get reimbursed—to the tune of $102,000 a student on average last year—was hire a lawyer.—
Marc Novicoff,
The Atlantic,
28 Apr. 2026
Verb
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Set one clear agreement, confirm who’s responsible, and follow through so everything stays consistent without needing to be reset later.—
Tarot.com,
Hartford Courant,
28 Apr. 2026
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By that point, with the Wild desperately needing a goal from somebody with their season on the line, coach John Hynes had loaded up the top line with Kirill Kaprizov, Joel Eriksson Ek and Boldy.—
Michael Russo,
New York Times,
27 Apr. 2026
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 1 May. 2026.
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