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Longman Dictionary of Contemporary English
rueful
adjective
COLLOCATIONS FROM OTHER ENTRIES
a rueful smilewritten (= when you feel slightly sad)
▪ ‘I’ve been pretty stupid, haven’t I?’ Harry said with a rueful smile.
COLLOCATIONS FROM CORPUS
■ NOUN
smile
▪ I shall never forget Jordi's face, his rueful smile, his fatalistic shrug as he was pushed into the car.
EXAMPLES FROM OTHER ENTRIES
▪ Jane looked at her with a rueful smile.
EXAMPLES FROM CORPUS
▪ Celia and Brassard, who had overheard everything from the outer office, exchanged rueful glances.
▪ Then she pulled a rueful face.
The Collaborative International Dictionary
Rueful

Rueful \Rue"ful\, a.

  1. Causing one to rue or lament; woeful; mournful; sorrowful.

  2. Expressing sorrow. ``Rueful faces.''
    --Dryden.

    Two rueful figures, with long black cloaks.
    --Sir W. Scott. [1913 Webster] -- Rue"ful*ly, adv. -- Rue"ful*ness, n.

Douglas Harper's Etymology Dictionary
rueful

early 13c., rewfulle, reowfule, from rue (n.2) + -ful. Related: Ruefulness.

Wiktionary
rueful

a. 1 Causing, feeling, or expressing regret or sorrow. 2 Inspiring pity or compassion.

WordNet
rueful

adj. feeling or expressing pain or sorrow for sins or offenses [syn: contrite, remorseful, ruthful, sorry]

Usage examples of "rueful".

Sam, looping girths over his arm, gave Tremayne a rueful smile and said Cashless had done his best.

I thought Arthur was about to make some comment comparing my present humble state with my future wealth and I was ready to defend Cwm Isaf against such a comparison, but instead he looked rueful.

She said the hah to herself with such force, it popped out of her mouth in the form of a rueful sigh.

Hazel, he observed with rueful bitterness, blowing air out through his teeth and pushing his hair back, - Ah might have tae move in thair masel, man.

One of them noticed Sile was awake and gave her a rueful shake of his head.

Tellis gave a rueful smile and motioned for Cerryl to follow him through the kitchen, past Beryal, who did not look up.

Iven cast her a rueful glance, knowing how much she had missed eating meat since joining company with the witches, and scrummaged in the store-barrels for something to throw the dogs.

Negrinus, with a flash of his understated intelligence, looked rueful, as if he knew exactly what I thought.

Lucille, who had been exchanging a few words with Therese and Simon Verey, looked rueful.

Merle Bowley stood beside an abashed and rueful Horseface Charley and regarded the dead man sprawled on the roadway, part of his head blown away by one of the large explosive rifle bullets.

He noted also with rueful pride that, despite the emission of the night, he was bearing before him as he left the kitchen, where he had eaten as well as cooked, a sizeable horizontal ithyphallus lazily swinging towards the vertical.

She had a rueful smile, and she pressed her hands together prayerlike, pleased.

Several of the directors chuckled and Etheridge had the grace to look rueful.

They were young, all those people gathered beyond the doorway, but haggard and slow to move, handymen, woodworkers, seamstresses, possessed of a rueful nostalgia, perhaps for the prairie womb common to them all, that land too bleak for song to live.

When they stopped, Gwendolyn looked up at Hildegard with a rueful expression.