doleful
[adjective]
Synonyms: downcast, cast down, crestfallen, dejected, depressed, dispirited, down, downhearted, down-in-the-mouth, woebegone, woeful, afflicted, dolent, dolorous, miserable, rueful, ruthful, sorrowful, wretched, melancholy, dolesome, lamentable, lugubrious, mournful, plaintive

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Antonyms: cheerful, cheery
Contrasted words: blithe, blithesome, radiant, sparkling, sunny
Related Words: grieving, mourning, sorrowing, piteous, pitiful

[TahlilGaran] English Synonym Dictionary ▲

dole‧ful /ˈdəʊlfəl $ ˈdoʊl-/ adjective formal
[Date: 1200-1300; Origin: dole 'sadness' (13-19 centuries), from Latin dolere 'to be sad']
very sad:
a doleful song about lost love
—dolefully adverb

[TahlilGaran] Dictionary of Contemporary English ▲