rueful

[roo-fuhl]
adjective
1.
causing sorrow or pity; pitiable; deplorable: a rueful plight.
2.
feeling, showing, or expressing sorrow or pity; mournful; doleful: the rueful look on her face.

Origin:
1175–1225; Middle English reowful. See rue1, -ful

ruefully, adverb
ruefulness, noun
half-rueful, adjective
half-ruefully, adverb
unrueful, adjective
unruefully, adverb
unruefulness, noun
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World English Dictionary
rueful (ˈruːfʊl)
 
adj
1.  feeling or expressing sorrow or repentance: a rueful face
2.  inspiring sorrow or pity
 
'ruefully
 
adv
 
'ruefulness
 
n

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

rueful
early 13c., rewfulle, reowfule, from rue (v.) + -ful.
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
Beneath the constant pep talks is a rueful sense of moral exhaustion.
Yet the movie and his performance have the retrospective air of rueful age.
His fiction runs the gamut, from rueful to riotously funny.
But handled with such humor, tenderness, and rueful wisdom that it's warming
  and enlightening rather than chilling or depressing.
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