dolesome adj.

late 13c., with -ful, from Middle English dole "emotion of grief, sorrow, lamentation, mourning" (early 13c., now archaic), from Old French doel (Modern French deuil), from Late Latin dolus "grief," from Latin dolere "suffer, grieve," which is of uncertain origin. De Vaan explains it as from PIE *dolh-eie- "to split" (source also of Middle Welsh e-thyl "chooses"), a causative verb from root *delh- "to chop," "under the assumption than 'pain' was expressed by the feeling of 'being torn apart'." Related: Dolefully; dolefulness.

word-forming element used in making adjectives from nouns or adjectives (and sometimes verbs) and meaning "tending to; causing; to a considerable degree," from Old English -sum, identical with some, from PIE root *sem- (1) "one; as one, together with." Cognate with Old Frisian -sum, German -sam, Old Norse -samr; also related to same.

"It usually indicates the possession of a considerable degree of the quality named: as mettlesome, full of mettle or spirit; gladsome, very glad or joyous" [Century Dictionary]. It is also, disguised, the ending in buxom. For the -some used with numbers (twosome, foursome, etc.), see -some (2).