doleful means filled with grief, mournful, bringing feelings of sadness.
doleful is pronounced /ˈdoʊlfəl/.
Why “doleful” is a great word
Filled with or expressing grief; mournful or sorrowful. From Middle English *doleful*, *doolful*, *deolful* (c. 1275), equivalent to *dole* ("grief, sorrow," from Old French *doel*, from Late Latin *dolus* "grief," from Latin *dolēre* "to grieve, suffer pain") + *-ful* ("full of"). Unlike "melancholy," which suggests a pensive, enduring, and often gentle sadness, or "lugubrious," which describes an exaggerated, theatrical gloom, *doleful* is straightforwardly and genuinely sorrowful. It is the single toll of a distant bell through mist, the slump of shoulders receiving bad news, the unwavering gaze of a dog by an empty chair—a sorrow worn plainly as the simple, burdensome truth, heavy and still as a hand upon a closed door.
Etymology
From Middle English doleful, doolful, deolful, equivalent to dole + -ful.
adj
- Filled with grief, mournful, bringing feelings of sadness.e.g.“The doleful peal of the bell indicated another funeral was being held.”
Words closest in meaning
By meaning, not spelling — each word's AI semantic fingerprint, nearest first.
- dolorous 93% match — Solemnly or ponderously sad. vs doleful →
- dolefulness 91% match — The characteristic of being doleful; sadness. vs doleful →
- dolour 90% match — Anguish, grief, misery, or sorrow. vs doleful →
- lugubrious 89% match — Gloomy, mournful or dismal, especially to an exaggerated degree. vs doleful →
- rueful 89% match — Causing, feeling, or expressing regret or sorrow, especially in a wry or humorous way. vs doleful →
- plaintive 89% match — Sounding sorrowful, mournful or melancholic. vs doleful →
- disconsolate 88% match — Cheerless, dreary. vs doleful →
- tristfulness 88% match — sadness; sorrow; melancholy vs doleful →