Doleful \Dole"ful\, a. Full of dole or grief; expressing or exciting sorrow; sorrowful; sad; dismal. [1913 Webster] With screwed face and doleful whine. --South. [1913 Webster] Regions of sorrow, doleful shades. --Milton. Syn: Piteous; rueful; sorrowful; woeful; melancholy; sad gloomy; dismal; dolorous; woe-begone. -- {Dole"ful*ly}, adv. -- {Dole"ful*ness}, n. [1913 Webster]