dole·ful

[dohl-fuhl]
adjective
sorrowful; mournful; melancholy: a doleful look on her face.

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

dole·ful·ly, adverb
dole·ful·ness, noun
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Based on the Random House Dictionary, © Random House, Inc. 2013.
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World English Dictionary
doleful (ˈdəʊlfʊl) [Click for IPA pronunciation guide]
 
adj
Archaic word: dolesome dreary; mournful
 
'dolefully
 
adv
 
'dolefulness
 
n

Collins English Dictionary - Complete & Unabridged 10th Edition
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00:10
Doleful is always a great word to know.
So is interrobang. Does it mean:
a printed punctuation mark (‽), available only in some typefaces, designed to combine the question mark (?) and the exclamation point (!), indicating a mixture of query and interjection, as after a rhetorical question.
a fool or simpleton; ninny.
Etymonline
Word Origin & History

doleful
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
We asked of each other's welfare, bemoaning our doleful condition and the
  change that had come upon us.
But in the basement the mood was anything but doleful.
Burnished doves moan their doleful love songs and young men's fancies turn.
Even a sad story does not seem quite so doleful in this context.
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