doleful (adj.) Look up doleful at
late 13c., with -ful, from Middle English dole "grief" (early 13c.), from Old French doel (Modern French deuil), from Late Latin dolus "grief," from Latin dolere "suffer, grieve," which is of uncertain origin. De Vaan reports that it can be derived from a PIE root *delh- "to chop" "under the assumption that 'pain' was expressed by the feeling of 'being torn apart'. A causative *dolh-eie- 'to make somebody (feel) split' could have become 'to cause pain'. The experiencer must originally have been expressed in the dative." Related: Dolefully.