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
Andrew Graham
april 21, Sacbee.com, 21 Apr. 2026
This elegant design was partly shaped by the constraints of the challenging site, which currently holds a hotel that will be demolished.
—Adam Williams
april 21, New Atlas, 21 Apr. 2026
Stephen Fowler, NPR, 23 Apr. 2026
Enbridge filed a separate federal lawsuit challenging the revocation.
—CBS News, 22 Apr. 2026
See All Example Sentences for challenging
Adjective
But the practicality of investigating federal officers, if Gabriel’s bill becomes law, could prove challenging.
—Andrew Graham
april 21, Sacbee.com, 21 Apr. 2026
This elegant design was partly shaped by the constraints of the challenging site, which currently holds a hotel that will be demolished.
—Adam Williams
april 21, New Atlas, 21 Apr. 2026
Verb
More money does not always guarantee success in challenging a sitting lawmaker, however.
—Stephen Fowler, NPR, 23 Apr. 2026
Enbridge filed a separate federal lawsuit challenging the revocation.
—CBS News, 22 Apr. 2026
See All Example Sentences for challenging
Recent Examples of Synonyms for challenging
Adjective
-
Putting in the new chip was more difficult.—
Julian Lucas,
New Yorker,
20 Apr. 2026
-
The rest will be more difficult.—
Doug Haller,
New York Times,
20 Apr. 2026
Adjective
-
The women farmers say that the demanding nature of the work in the chile pepper fields discourages men.—
Suzanne Nuyen,
NPR,
20 Apr. 2026
-
What follows this war will be narrower, harder, and more demanding.—
Nawaf M. Al-Thani,
semafor.com,
20 Apr. 2026
Verb
-
Sources say the character didn’t survive test screenings (audiences kept questioning why Andy needed a roommate at all).—
Kennedy French,
Variety,
21 Apr. 2026
-
Panamanian officials confirmed that Jalil was immediately transferred to the country’s Judicial Investigation Directorate and is expected to face questioning by prosecutors in the coming days.—
Antonio María Delgado,
Miami Herald,
21 Apr. 2026
Verb
-
Elsewhere on the menu, coconut and tamarind flavors mingle, producing fusion-style flavors that push dishes just to the edge, enough to be daring but not too much to alienate diners.—
Michael James Rocha,
San Diego Union-Tribune,
10 Apr. 2026
-
His own series of daring explorations.—
Courtney Crowder,
USA Today,
10 Apr. 2026
Verb
-
The moderate’s vision may even be the harder one to sustain, requiring a tolerance for frustration and an inurement to defeat and political disappointment.—
Nikhil Krishnan,
New Yorker,
20 Apr. 2026
-
New York City has already banned gas stoves and furnaces in new buildings, and Albany is moving to copy California’s approach by requiring zero-emission vehicles for future car, pickup, and SUV sales.—
Nicole Malliotakis,
New York Daily News,
19 Apr. 2026
Adjective
-
That's a tough ask given that this isn't the first time the network's credibility has come into question.—
Dan Zaksheske OutKick,
FOXNews.com,
23 Apr. 2026
-
Another tough one, all having to do with writer friends and boundaries (or the lack thereof).—
Literary Hub,
Literary Hub,
23 Apr. 2026
Verb
-
Anthony Edwards was the low man, contesting the shot for Minnesota.—
Bennett Durando,
Denver Post,
21 Apr. 2026
-
But Mike’s attorney, Raymond Rafool, tells PEOPLE that Constance is contesting that, likening it to a bad deal signed years ago at a vulnerable moment.—
David Chiu,
PEOPLE,
16 Apr. 2026
Verb
-
Spurs must somehow move on from the palpable devastation that left Kevin Danso on the floor, needing to be pulled up by his team-mates, and other players looking utterly crestfallen at the final whistle.—
Jack Pitt-Brooke,
New York Times,
20 Apr. 2026
-
Other signs that warrant seeing a doctor include blood in the stool or a persistent feeling of needing to go to the bathroom but being unable to go.—
Khloe Quill,
FOXNews.com,
20 Apr. 2026
Cite this Entry
“Challenging.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/challenging. Accessed 24 Apr. 2026.
Copy CitationLove words? Need even more definitions?
Merriam-Webster unabridged
