sorrowful; mournful; melancholy: a doleful look on her face.

1225–75; Middle English dol-ful. See dole2, -ful

dolefully, adverb
dolefulness, noun Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2014.
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World English Dictionary
doleful (ˈdəʊlfʊl)
Archaic word: dolesome dreary; mournful

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
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Word Origin & History

late 13c., from O.Fr. doel, from L.L. dolus "grief," from L. dolere "suffer, grieve." Related: Dolefully.
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
Cullers adjusts his cap and stares off into the distance dolefully-trapped, it seems, by his own success.
There they hung yet, every rusty link squeaking dolefully in the wind that never ceased blowing from the sea.
Dolefully, with every blast, peace looks more distant.
He is a poor lost hound dog dolefully pining for his master's forgiveness.
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