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
Synonyms & Similar Words
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
-
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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Conservative critics seized upon those allegations, accusing Hosseini of exerting outsized influence over UF’s presidential search process and questioning whether trustees had exercised independent judgment in selecting Bell.
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What immediately followed that bright June day were dark months marred by the state’s largest criminal investigation in history coming up empty, police questioning second graders for new leads and mounting legal battles among the Horman family grappling with utter devastation.
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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Millions of index cards, once restricted by German privacy laws and requiring a lengthy process to obtain, are now directly searchable online in German media, as of a few months ago, after the US National Archives published the surviving membership card files online.
-
But the fact is that a medium-sized power at this point is perceived to have fought a superpower to a draw, requiring some measure of accommodation of we, the superpower.
Adjective
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Summer 2026 is having a tough time deciding on this season’s dominating nail trend.
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These are typically low-wage jobs that the healthcare industry writ large has had a tough time recruiting for since the pandemic.
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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Almost all patients required hospitalization, with roughly two-thirds of those admitted needing intensive care.
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La Celeste face Spain in their group stage finale, needing a positive result to have a chance at advancing.
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 30 Jun. 2026.
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