Full of grief or sorrow; expressing pain, sadness, or regret. Characterized by a mournful or melancholy quality.
From Middle English 'dole' meaning grief or sorrow, plus the suffix '-ful.' 'Dole' comes from Old French 'dol,' meaning pain or grief, ultimately from Latin 'dolere' (to suffer).
Remember 'dole' as in 'doling out' sadness - when someone is doleful, they're literally full of dole (grief), as if sadness has been measured out and poured into them until they're brimming with sorrow.
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