rueful

• ruefull (obsolete)

From Middle English ruful, rewful. By surface analysis, rue +‎ -ful.

• IPA^(key): /ˈɹuːfl̩/

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rueful (comparative more rueful, superlative most rueful)

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

   Synonyms: deplorable, pitiful, sorry; see also Thesaurus:lamentable, Thesaurus:regretful

   • 1986, John le Carré, A Perfect Spy:

     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.

2. Inspiring pity or compassion.

   Synonyms: pathetic, pitiable, pitiful, pitisome; see also Thesaurus:pitiful

3. Bad; woeful; deplorable.

   Synonyms: unfavorable, negative; see also Thesaurus:bad

• rue