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
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
Wallen is constantly trying to find new ways to navigate the tension between pleasure and piety, Saturday night and Sunday morning, his horniness and his self-loathing—already the grist for a thousand doleful ballads.
—Amanda Petrusich, New Yorker, 16 May 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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Michael Phillips, Chicago Tribune, 19 June 2025
Wallen is constantly trying to find new ways to navigate the tension between pleasure and piety, Saturday night and Sunday morning, his horniness and his self-loathing—already the grist for a thousand doleful ballads.
—Amanda Petrusich, New Yorker, 16 May 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 31 Oct. 2025.
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