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
Tanaya MacHeel,
CNBC,
24 June 2026
After a challenging Pitti and Milan due to the high temperatures, Paris Men’s Week takes place from June 23 to 28 against the backdrop of what could be the hottest week in France’s history.
—
Laure Guilbault,
Vogue,
23 June 2026
Nina Totenberg,
NPR,
25 June 2026
Instead of highlighting a spot for a radiologist to review and write up, generative AI can process the entire image and draft many of its findings for a radiologist to review — a technological advancement that is challenging traditional validation and regulatory frameworks.
—
Katie Palmer,
STAT,
25 June 2026
See All Example Sentences for challenging
Adjective
Meanwhile, inflationary pressures stemming from the Iran war have kept the Federal Reserve focused on combating inflation, creating a challenging backdrop for bitcoin.
—
Tanaya MacHeel,
CNBC,
24 June 2026
After a challenging Pitti and Milan due to the high temperatures, Paris Men’s Week takes place from June 23 to 28 against the backdrop of what could be the hottest week in France’s history.
—
Laure Guilbault,
Vogue,
23 June 2026
Verb
The Supreme Court sided with those challenging the laws barring guns on private property.
—
Nina Totenberg,
NPR,
25 June 2026
Instead of highlighting a spot for a radiologist to review and write up, generative AI can process the entire image and draft many of its findings for a radiologist to review — a technological advancement that is challenging traditional validation and regulatory frameworks.
—
Katie Palmer,
STAT,
25 June 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
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Aviation experts said those conditions would have been difficult to navigate that evening when the helicopter, a Robinson R66, crashed in the Dawson Forest Wildlife Management Area.
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But traffic on the waterway remains a fraction of pre-war levels with different authorities vying to organize the transit of vessels, leaving operators with a difficult choice over which path to take.
Adjective
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In a demanding, real-world performance setting — a capstone exercise, a live performance, a high-stakes simulation — the goal is not to eliminate all mistakes, but to stay in control and navigate the zone of being uncomfortable.
-
New York crowds are passionate, honest, and demanding.
Verb
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The video ends with the woman remaining at the scene until Broward Sheriff's Office deputies arrived and detained her for questioning.
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This can be especially true for LGBTQ+ youth looking for support, teens questioning their identity, or young people whose religious, political or social views differ from those of their parents.
Verb
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One by one, daring participants dash across a 45-foot horizontal telephone pole that's coated in grease, attempting to capture a flag at the end of it.
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Versace isn't one of the world's most famous fashion houses thanks to its subtlety, and the brand's swimsuits are just as bright, bold, and daring as its couture and ready-to-wear collections.
Verb
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Those decisions on what to review next in the Second Amendment space come after the high court struck down on June 25 a Hawaii law requiring gun owners to get permission before bringing guns into stores or other private property open to the public.
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The findings suggest that requiring face mask use in public could help in mitigating the spread of COVID-19.
Adjective
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MacDonald agrees that some of Kiros' positions could put Democratic candidates in a tough spot.
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The 34 measures include cuts to income tax for low- and middle income families, an overhaul of the creaking pension system, tougher rules for employees' sick leave and a reduction of the country's stifling bureaucracy.
Verb
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Unless his future is resolved before then, the Egypt captain could find himself in the unusual position of contesting a World Cup knockout match without being tied to any club.
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Regulators are now writing rules for a sanctioned technology rather than contesting whether it should be permitted at all.
Verb
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January 20 – February 18 Connections feel electric without needing to rush.
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Amiri came up next, needing to score to keep his team alive and simply buried it in the bottom right corner.
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 3 Jul. 2026.
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