rueful

[ roo-fuh l ]

/ ˈru fəl /

causing sorrow or pity; pitiable; deplorable: a rueful plight.

feeling, showing, or expressing sorrow or pity; mournful; doleful: the rueful look on her face.

Origin of rueful

First recorded in 1175–1225, rueful is from the Middle English word reowful. See rue¹, -ful

rue·ful·ly, adverb rue·ful·ness, noun half-rue·ful, adjective half-rue·ful·ly, adverb

un·rue·ful, adjective un·rue·ful·ly, adverb un·rue·ful·ness, noun

rudy, rudyard, rue, rue anemone, rue family, rueful, rufen, rufescent, ruff, ruffe, ruffed

Rueful laughter from both men turned to thoughtfulness in Stittsworth.

The Strange, True Tale of the Old-Timey Goat Testicle-Implanting 'Governor' |Penny Lane |September 16, 2014 |DAILY BEAST
You can only ever see it from an outsider and comment on it with the rueful wisdom of a non participant.

Benedict Cumberbatch’s Revealing Reddit AMA: On Julian Assange’s Letter and Fame |Marlow Stern |October 11, 2013 |DAILY BEAST
A discussion of a London cheese shop sends her into paroxysms of rueful joy.

Michelle Forbes' Good Grief |Jace Lacob |May 22, 2011 |DAILY BEAST
But most of them must be delivered from on the peninsula, where Bob is standing, casting a rueful eye on the whole show.

On the Peninsula |Bryan Curtis |April 25, 2011 |DAILY BEAST

“You can pick which lines can come out,” Spitzer said with a rueful smile.

Eliot Spitzer's Comeback Trail |Lloyd Grove |May 10, 2010 |DAILY BEAST
The muscles of the woman's face twisted it into a rueful smile.

The Dawn of a To-morrow |Frances Hodgson Burnett
Hilbrough acquiesced with a rueful sense that he should be clumsy enough at entertaining a foreigner and a man of title.

The Faith Doctor |Edward Eggleston
Benjamin looked down again at his plate, with a rueful resignation which told me that I had carried my point.

The Law and the Lady |Wilkie Collins
The comment was dragged from Jeannette in a tone as unconsciously reluctant as his was rueful.

Golden Stories |Various
He rose to his feet and paid his bill with a rueful conviction that he had fought not wisely, though so well.

The Mayor of Warwick |Herbert M. Hopkins

rueful

/ (ˈruːfʊl) /

feeling or expressing sorrow or repentance a rueful face

inspiring sorrow or pity

ruefully, adverb ruefulness, noun