'dolefully' originates from English, specifically from the adjective 'doleful', which itself is formed from 'dole' where the root meant 'sorrow or grief'.

'doleful' developed in Middle English from 'dole' + the suffix '-ful'; 'dole' comes from Old English 'dolu' meaning 'sorrow, grief'. The adverb 'dolefully' formed by adding the adverbial suffix '-ly' to 'doleful'.

Initially it meant 'full of sorrow' (applied to a person or expression); over time it has been used as an adverb to mean 'in a sorrowful or mournful manner'.