showing the wearing effects of overwork or care or suffering; "looking careworn as she bent over her mending"; "her face was drawn and haggard from sleeplessness"; "that raddled but still noble face"; "shocked to see the worn look of his handsome young face"- Charles Dickens
experiencing intense pain especially mental pain; "an anguished conscience"; "a small tormented schoolboy"; "a tortured witness to another's humiliation"
experiencing or marked by or expressing sorrow especially that associated with irreparable loss; "sorrowful widows"; "a sorrowful tale of death and despair"; "sorrowful news"; "even in laughter the heart is sorrowful"- Proverbs 14:13
causing or marked by grief or anguish; "a grievous loss"; "a grievous cry"; "her sigh was heartbreaking"; "the heartrending words of Rabin's granddaughter"