Synonyms of heartbreaking

1 Syllable
sad, dire
2 Syllables
touching, joyless, poignant, grievous, stirring, ruthful, piteous, woeful, tragic, cheerless, bitter, moving
3 Syllables
pitiable, pitiful, heart-rending, distressing, pathetic, harrowing, heartrending, mind-bending, godawful, depressing, affecting
4 Syllables
lamentable, deplorable, calamitous, regrettable, agonizing, afflictive
5 Syllables
unfortunate, stimulative, inspirational, commiserable