dolorous (adj.)

• affecting
• afflicted
• afflictive
• anguished
• bitter
• bleak
• calamitous
• careworn
• cheerless
• comfortless
• deplorable
• depressing
• depressive
• dire
• dismal
• dismaying
• distressful
• distressing
• doleful
• dreary
• grief-stricken
• grievous
• heartbreaking
• joyless
• lamentable
• lugubrious
• miserable
• mournful
• moving
• painful
• pathetic
• piteous
• pitiable
• plaintive
• plangent
• poignant
• regrettable
• rueful
• ruthful
• sad
• sharp
• sore
• sorrowful
• sorrowing
• tearful
• touching
• uncomfortable
• woebegone
• woeful
• wretched