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
Examples are automatically compiled from online sources to
show current usage.
Read More
Opinions expressed in the examples do not represent those of Merriam-Webster or its editors.
Send us feedback.
Recent Examples of challenging
Ishani Desai, Sacbee.com, 6 May 2026
Leaders across the globe called on Iran Monday evening to de-escalate tensions in the Middle East after the country launched attacks on the United Arab Emirates, putting the ceasefire agreement to its most challenging test yet.
—Christopher Cann, USA Today, 5 May 2026
Alice Xiang, Time, 6 May 2026
Although there were plenty of milestones to celebrate, the path was long and challenging for the new parents.
—Paloma Chavez, PEOPLE, 6 May 2026
See All Example Sentences for challenging
Adjective
If so, what has been the most challenging aspect?
—Ishani Desai, Sacbee.com, 6 May 2026
Leaders across the globe called on Iran Monday evening to de-escalate tensions in the Middle East after the country launched attacks on the United Arab Emirates, putting the ceasefire agreement to its most challenging test yet.
—Christopher Cann, USA Today, 5 May 2026
Verb
In parallel, a wave of litigation under privacy laws like Illinois’s Biometric Information Privacy Act (BIPA) is challenging the unauthorized use of our most personal data—our faces and voices.
—Alice Xiang, Time, 6 May 2026
Although there were plenty of milestones to celebrate, the path was long and challenging for the new parents.
—Paloma Chavez, PEOPLE, 6 May 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
-
The Aces scored 26 points off those giveaways, which made things even more difficult on the defense.—
Marisa Ingemi,
Los Angeles Times,
11 May 2026
-
Schiraldi oversaw a particularly difficult period on Rikers.—
Molly Fischer,
New Yorker,
11 May 2026
Adjective
-
Inspired by their connection, Étienne contemplates exchanging his lonely existence for one filled with romance, but with a demanding route to cover, starring in a great love story may not be in the cards for the hard-working road warrior.—
Elaina Patton,
IndieWire,
12 May 2026
-
Paro International Airport in Bhutan is one of the world’s most technically demanding, with only about 50 certified pilots navigating its mountainous approach.—
Chris Dong,
Travel + Leisure,
12 May 2026
Verb
-
At a recent town hall, that concern was raised directly, The Phoenix reported, with some alumni and community members questioning whether removing Trotter’s name constitutes revisionism.—
Stepheny Price,
FOXNews.com,
12 May 2026
-
She was criticized publicly by some colleagues as well anonymous government officials who were quoted in Israeli and international media questioning her motives.—
Ivana Kottasová,
CNN Money,
12 May 2026
Verb
-
Opposing pitchers are attacking the Giants’ hitters and daring them to make contact.—
Justice delos Santos,
Mercury News,
9 May 2026
-
Crocodile suspected of eating local man airlifted in daring mission to retrieve remains.—
,
FOXNews.com,
6 May 2026
Verb
-
Critics say the commission lacks religious and ideological diversity, violates federal law requiring balanced viewpoints, and threatens long-standing constitutional church-state protections.—
Peter Smith,
Los Angeles Times,
10 May 2026
-
These material queries can be performed on a standard desktop computer rather than requiring expensive supercomputer calculations.—
Aman Tripathi,
Interesting Engineering,
10 May 2026
Adjective
-
Chase Meidroth made a shuffle toss to second base for a force out, but the Sox couldn’t complete what would have been a tough double play.—
LaMond Pope,
Chicago Tribune,
7 May 2026
-
Our legislators must make some tough decisions; avoiding the issues is not acceptable.—
Lucas Robinson,
San Diego Union-Tribune,
7 May 2026
Verb
-
Democrats were not calling for contesting War Powers Resolution and what the executive power was there.—
NBC news,
NBC news,
3 May 2026
-
So your rotations aren’t just about contesting 3s.—
Bennett Durando,
Denver Post,
30 Apr. 2026
Verb
-
The day after that loss, per team sources, Brunson approached the team before practice about needing to re-shift the collective mindset.—
James L. Edwards III,
New York Times,
11 May 2026
-
Galeno is licensed to keep Drago the alligator until the reptile is ready and maybe too big, needing relocation to a proper environment for alligators of his size.—
Karie Angell Luc,
Chicago Tribune,
11 May 2026
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 13 May. 2026.
Copy CitationLove words? Need even more definitions?
Merriam-Webster unabridged
