From Longman Dictionary of Contemporary Englishdolefuldole‧ful /ˈdəʊlfəl $ ˈdoʊl-/ adjective formal SAD/UNHAPPYvery sad a doleful song about lost love —dolefully adverb
Examples from the Corpus
doleful• Baudelaire curled up on the chintz sofa and looked doleful.• Everyman wasn't as comprehensive and incisive as it might have been, but it was an intriguing, doleful documentary none the less.• a doleful look• There was never anything sophisticated or subtle about the doleful northerner but boy, could he make you laugh.• Yet the reading appeared to bring Emilia a kind of doleful peace.• So it was doubly doleful to me.Origin doleful (1200-1300) dole “sadness” ((13-19 centuries)), from Latin dolere “to be sad” 