Entry 1 sense Webster, 1913 Doleful /dōl'-fəl/ · Dole·ful · IPA /ˈdoʊlfəl/ 01 a. Full of dole or grief; expressing or exciting sorrow; sorrowful; sad; dismal. 1. Full of dole or grief; expressing or exciting sorrow; sorrowful; sad; dismal. “With screwed face and doleful whine.” — South. “Regions of sorrow, doleful shades.” — Milton. Syn. Piteous; rueful; sorrowful; woeful; melancholy; sad gloomy; dismal; dolorous; woe-begone.