rueful

comparative more rueful · superlative most rueful · alternative obsolete ruefull

1. Causing, feeling, or expressing regret or sorrow, especially in a wry or humorous way.

   Merely, he received it with the rueful indulgence that he would show towards Tom when he came through with one of his solutions for ending world poverty or the arms race.

   1986, John le Carré, A Perfect Spy

   1 more example

   "I like the young, andro look, but I've dated across the board—butches, femmes, trannies—and that really bothers Clara. All her girlfriends in the past have been pretty much straight." Kim offers a rueful little laugh.

   2004, New York

   Synonyms: deplorable, pitiful, sorry, atrabiliary, atrabilious, deplorable, depressing, distressing

2. Inspiring pity or compassion.

   Synonyms: pathetic, pitiable, pitiful, pitisome, compassionate, pathetic, pathetisad, piteous

3. Bad; woeful; deplorable.

   1 more example

   The first who made the experiment was a merry-andrew, who was put into my hands by a neighbouring justice of peace, in order to reclaim him from that profligate kind of life. Poor Pickle-herring had not taken above one turn in it, when he came out of the cave, like a hermit from his cell, with a penitential look and a most rueful countenance.

   1714 September 24 (Gregorian calendar), [Joseph Addison], “MONDAY, September 14, 1714”, in The Spectator, number 599; republished in Alexander Chalmers, editor, The Spectator; a New Edition, […], volume VI, New York, N.Y.: D[aniel] Appleton & Company, 1853, →OCLC

   Synonyms: unfavorable, negative, abysmal, atrocious, awful, bad, chronic, coarse