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
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
Her Night Moves may have been a thriller, though its focus was less the act of environmental sabotage that its characters carried out than its doleful aftermath.
—Alison Willmore, Vulture, 13 May 2025
James, with his doleful countenance, makes the adult Hal vaguely sympathetic.
—Owen Gleiberman, Variety, 17 Feb. 2025
See All Example Sentences for doleful
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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
Her Night Moves may have been a thriller, though its focus was less the act of environmental sabotage that its characters carried out than its doleful aftermath.
—Alison Willmore, Vulture, 13 May 2025
James, with his doleful countenance, makes the adult Hal vaguely sympathetic.
—Owen Gleiberman, Variety, 17 Feb. 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 7 Nov. 2025.
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