ruful

Adjective

rueful (comparative more rueful, superlative most rueful)

1. Causing, feeling, or expressing regret or sorrow, especially in a wry or humorous way.
   • "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, depressing, distressing, grievous, heartbreaking, heartrending

2. Inspiring pity or compassion.

   Synonyms:

   pathetic, pitiable, pitiful, pitisome, compassionate, pathetisad, piteous, sad, poor, ruthful

3. Bad; woeful; deplorable.
   • 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...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, […]...

   Synonyms:

   unfavorable, negative, abysmal, atrocious, awful, bad, chronic, coarse, corny, crap