1
: full of grief : cheerless
a doleful face
2
: expressing grief : sad
a doleful melody
3
: causing grief or affliction
a doleful loss
dolefulness
noun
Examples of doleful in a Sentence
The girl had a doleful look on her face.
You sounded so doleful about your future that night.
Recent Examples on the Web
The Canadian filmmaker Sophy Romvari does something similar with the new movie Blue Heron, a semi-autobiographical piece whose structure loops in on itself, melding fact and fiction into a doleful portrait of a family tragedy.
—
Richard Lawson, HollywoodReporter, 16 Apr. 2026
Black Hills bucket-listing aside, time here is best spent tubing and fishing on the river, luxuriating in the infrared sauna, or listening to a doleful coyote song under a blanket of stars.
—Ashlea Halpern, Time, 12 Mar. 2026
With their large hands and expressive, doleful faces, the great apes are often depicted as the poster children for experimentation.
—Ava Kofman, New Yorker, 3 Nov. 2025
His doleful father, portrayed by Paul Dooley in a magically right match of performer and material, despairs for his blithely romantic son’s future.
—Michael Phillips, Chicago Tribune, 19 June 2025
See All Example Sentences for doleful
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Richard Lawson, HollywoodReporter, 16 Apr. 2026
Black Hills bucket-listing aside, time here is best spent tubing and fishing on the river, luxuriating in the infrared sauna, or listening to a doleful coyote song under a blanket of stars.
—Ashlea Halpern, Time, 12 Mar. 2026
With their large hands and expressive, doleful faces, the great apes are often depicted as the poster children for experimentation.
—Ava Kofman, New Yorker, 3 Nov. 2025
His doleful father, portrayed by Paul Dooley in a magically right match of performer and material, despairs for his blithely romantic son’s future.
—Michael Phillips, Chicago Tribune, 19 June 2025
See All Example Sentences for doleful
Cite this Entry
“Doleful.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/doleful. Accessed 22 Apr. 2026.
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