'cheerlessness' originates from English, specifically the word 'cheerless' plus the noun-forming suffix '-ness', where 'cheer' originally meant 'face, expression' and later 'mood; encouragement', '-less' meant 'without', and '-ness' formed a noun meaning 'state or quality'.

'cheerlessness' developed from Middle English 'chere' (from Old French 'chere', meaning 'face, expression'), which became English 'cheer' meaning 'mood' or 'encouragement'; the adjective 'cheerless' (cheer + -less) arose in later Middle English, and the abstract noun 'cheerlessness' was formed by adding '-ness'.

Initially 'cheer' referred to the face or expression; over time it shifted to mean 'mood' or 'encouragement', and 'cheerlessness' came to mean the absence of cheer or a state of gloom.