| No. | Item | Definition |
|---|---|---|
| 1. | aching | full of deep pain |
| 2. | affecting | emotionally moving or sad |
| 3. | agonizing | causing intense suffering |
| 4. | anguishing | causing severe emotional pain |
| 5. | appalling | deeply upsetting or shocking |
| 6. | awful | very bad and upsetting |
| 7. | bereft | deprived and grieving |
| 8. | bitter | sharply painful and sad |
| 9. | bleak | hopelessly sad or grim |
| 10. | blue | sad or melancholy |
| 11. | broken | emotionally shattered |
| 12. | brokenhearted | overwhelmed by emotional grief |
| 13. | brutal | harshly painful or upsetting |
| 14. | calamitous | disastrously sad or harmful |
| 15. | catastrophic | ruinously bad and upsetting |
| 16. | cheerless | without comfort or joy |
| 17. | comfortless | without consolation or hope |
| 18. | crushing | causing intense emotional pain |
| 19. | demoralizing | destroying confidence or spirit |
| 20. | depressing | making you feel very sad |
| 21. | despair-inducing | causing hopeless sadness |
| 22. | despairing | without hope and deeply sad |
| 23. | devastating | causing overwhelming sadness or shock |
| 24. | disheartening | causing loss of hope |
| 25. | dismal | gloomy and deeply discouraging |
| 26. | dispiriting | causing loss of hope |
| 27. | distressing | causing anxiety or sorrow |
| 28. | dreadful | causing great fear or sadness |
| 29. | excruciating | extremely painful emotionally |
| 30. | fatal | ending in death or ruin |
| 31. | forlorn | sad and lonely |
| 32. | funereal | suggesting death and mourning |
| 33. | ghastly | shockingly dreadful and upsetting |
| 34. | gloomy | darkly sad or depressing |
| 35. | grave | serious and deeply sad |
| 36. | grief-filled | full of grief |
| 37. | grief-stricken | overcome with grief |
| 38. | grievous | causing deep sorrow |
| 39. | grim | harshly sad or hopeless |
| 40. | gut-wrenching | causing intense emotional anguish |
| 41. | harrowing | extremely distressing and painful |
| 42. | haunting | staying painfully in memory |
| 43. | hauntingly sad | memorably and deeply sad |
| 44. | heart-rending | causing deep sorrow |
| 45. | heart-wrenching | causing deep emotional pain |
| 46. | heartsick | deeply unhappy or distressed |
| 47. | heartsore | sorrowfully hurt |
| 48. | hopeless | without hope or comfort |
| 49. | horrific | terribly shocking and upsetting |
| 50. | horrifying | causing horror and distress |
| 51. | ill-fated | marked by tragic misfortune |
| 52. | ill-starred | unluckily doomed or tragic |
| 53. | intolerable | impossible to bear emotionally |
| 54. | jolting | causing sudden emotional shock |
| 55. | joyless | without happiness |
| 56. | lacerating | causing deep emotional pain |
| 57. | lamentable | deserving sorrow or regret |
| 58. | melancholy | sad and reflective |
| 59. | miserable | causing or showing misery |
| 60. | mournful | expressing deep sadness |
| 61. | mournsome | sad and mournful |
| 62. | moving | deeply affecting emotionally |
| 63. | nightmarish | frighteningly distressing |
| 64. | oppressive | heavily distressing |
| 65. | painful | causing emotional hurt |
| 66. | pathetic | arousing pity and sadness |
| 67. | piercing | sharply painful emotionally |
| 68. | piteous | deserving pity and sorrow |
| 69. | pitiful | arousing sympathy and sadness |
| 70. | plaintive | sadly expressive or mournful |
| 71. | poignant | evoking sadness and tenderness |
| 72. | raw | painfully exposed emotionally |
| 73. | regrettable | causing sadness or disappointment |
| 74. | rending | tearing emotionally |
| 75. | ruinous | causing severe emotional damage |
| 76. | saddening | making you feel sad |
| 77. | shattering | emotionally crushing and upsetting |
| 78. | shocking | causing emotional shock |
| 79. | sorrowful | full of sorrow |
| 80. | soul-crushing | destroying hope or spirit |
| 81. | soul-destroying | ruining spirit or hope |
| 82. | soul-sapping | draining spirit and hope |
| 83. | spirit-breaking | destroying courage or hope |
| 84. | star-crossed | doomed by fate in love |
| 85. | tear-jerking | making people cry |
| 86. | terrible | extremely bad and upsetting |
| 87. | tormenting | causing mental anguish |
| 88. | touching | causing tender sadness |
| 89. | tragic | deeply sad and disastrous |
| 90. | tragical | tragic and deeply sad |
| 91. | traumatic | emotionally shocking and painful |
| 92. | troubling | causing worry and sadness |
| 93. | unbearable | too painful to endure |
| 94. | unfortunate | sadly unlucky or regrettable |
| 95. | unsettling | making you feel disturbed |
| 96. | woe-stricken | struck by sorrow |
| 97. | woebegone | showing great sorrow |
| 98. | woeful | full of sorrow or misery |
| 99. | wrenching | causing deep emotional pain |
| 100. | wretched | deeply unhappy or pitiful |
