rueful means causing, feeling, or expressing regret or sorrow, especially in a wry or humorous way.
rueful is pronounced /ˈɹuːfl̩/.
Why “rueful” is a great word
A feeling or expression of regret or sorrow, often with a wry or humorous acceptance. From the Middle English *rewe* (sorrow, regret), from the Old English *hrēow* (sorrow, regret, penitence), from the Proto-Germanic *hrewō*, related to the Old English verb *hrēowan* (to affect with grief, to rue). Unlike "remorseful" (which implies a sharper, more anguished guilt) or "lamentable" (which colors the event itself), "rueful" colors the countenance. It is the slow shake of a head over a self-inflicted folly, the crooked smile that accompanies a lost bet, the quiet sigh released into the stillness of an empty room—the elegant, slightly comic posture we assume when we meet the consequences of our own imperfect choices.
adj
- 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.”
- Inspiring pity or compassion.
- 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 penitential look and a most rueful countenance.”
Words closest in meaning
By meaning, not spelling — each word's AI semantic fingerprint, nearest first.
- remorse 88% match — A feeling of regret or sadness for doing wrong or sinning. vs rueful →
- mourn 86% match — To express sadness or sorrow for; to grieve over (especially a death). vs rueful →
- commiserate 86% match — Commiserating, pitying, lamentful. vs rueful →
- bewail 86% match — To wail over; to feel or express deep sorrow for. vs rueful →
- alas 86% match — Used to express sorrow, regret, compassion, grief, resignation, or disappointment. vs rueful →
- ruthfulness 86% match — The state or condition of being ruthful; sorrowfulness; contrition. vs rueful →
- compunction 86% match — A pricking of conscience or a feeling of regret, especially one which is slight or fleeting. vs rueful →
- bemoan 85% match — To moan or complain about (something). vs rueful →