Characterized by or causing sorrow, sadness, or melancholy; mournful, sorrowful, and dreary; like or full of dole (grief).
From dole (sorrow, grief) + -some (adjective suffix meaning full of or characterized by). This formation parallels other -some adjectives like 'tiresome' or 'gladsome,' though 'dolesome' is archaic.
The -some suffix created wonderful old English words like 'fulsome,' 'lonesome,' and 'dolesome'—they sound almost Shakespearean because they were more common in Early Modern English, before we started preferring Latin-derived forms.
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