| No. | Item | Definition |
|---|---|---|
| 1. | abysmal | extremely bad or hopeless |
| 2. | afflicted | suffering pain or distress |
| 3. | agonizing | causing intense emotional pain |
| 4. | anguished | showing severe mental pain |
| 5. | appalling | shocking and very bad |
| 6. | atrocious | shockingly bad or awful |
| 7. | baleful | threatening harm or misery |
| 8. | bereft | deprived and grief-filled |
| 9. | blasted | ruined or devastated |
| 10. | bleak | without hope or comfort |
| 11. | blighted | ruined or spoiled sadly |
| 12. | brokenhearted | overwhelmed by grief |
| 13. | calamitous | bringing great disaster or misery |
| 14. | calamity-struck | hit by disaster or misery |
| 15. | cataclysmic | causing violent, disastrous change |
| 16. | catastrophic | disastrously bad or ruinous |
| 17. | crestfallen | sadly disappointed and downcast |
| 18. | crushing | overwhelmingly disappointing or sad |
| 19. | deplorable | very bad and lamentable |
| 20. | desolate | empty, hopeless, and sad |
| 21. | devastating | extremely damaging or upsetting |
| 22. | dire | extremely serious or dreadful |
| 23. | disastrous | causing great harm or sorrow |
| 24. | dismal | gloomy, bleak, and depressing |
| 25. | distressing | causing anxiety, sorrow, or pain |
| 26. | doomed | certain to end badly |
| 27. | dreadful | very bad and distressing |
| 28. | elegiac | sadly reflective about loss |
| 29. | execrable | extremely bad and lamentable |
| 30. | fatal | causing death or disaster |
| 31. | fateful | having serious, disastrous consequences |
| 32. | forlorn | pitifully sad and abandoned |
| 33. | ghastly | frighteningly bad or shocking |
| 34. | gloomy | dark, sad, or hopeless |
| 35. | grief-filled | full of grief |
| 36. | grief-laden | heavy with grief |
| 37. | grief-stricken | suffering intense grief |
| 38. | grievous | causing severe pain or sorrow |
| 39. | grim | bleak and deeply serious |
| 40. | gut-wrenching | causing intense emotional distress |
| 41. | hapless | unlucky and unfortunate |
| 42. | harrowing | deeply distressing or disturbing |
| 43. | heart-wrenching | causing intense emotional pain |
| 44. | heartbreaking | causing deep sadness or grief |
| 45. | heartrending | causing intense sorrow |
| 46. | hopeless | without hope of improvement |
| 47. | horrible | very unpleasant or distressing |
| 48. | horrific | causing horror or great distress |
| 49. | ill-fated | doomed to bad outcomes |
| 50. | ill-omened | suggesting bad outcomes |
| 51. | ill-starred | marked by bad luck |
| 52. | inauspicious | unfavorable and unlucky |
| 53. | indescribable | too extreme to describe |
| 54. | insufferable | too severe to bear |
| 55. | intolerable | impossible to endure calmly |
| 56. | lamentable | deserving sorrow or regret |
| 57. | luckless | having bad luck |
| 58. | lugubrious | excessively mournful or gloomy |
| 59. | melancholy | sad and thoughtful |
| 60. | miserable | extremely unhappy or distressing |
| 61. | misfortunate | unfortunate in a sad way |
| 62. | mournful | expressing sadness or grief |
| 63. | mourning | feeling grief after loss |
| 64. | mournsome | causing or expressing mourning |
| 65. | moving | deeply affecting and sad |
| 66. | nightmarish | like a terrible nightmare |
| 67. | ominous | suggesting something bad ahead |
| 68. | painful | emotionally hard to bear |
| 69. | pathetic | arousing pity or sadness |
| 70. | pitiful | arousing sadness or pity |
| 71. | poignant | deeply affecting and sad |
| 72. | regrettable | causing sorrow or disappointment |
| 73. | ruined | destroyed or severely harmed |
| 74. | ruinous | causing destruction or disaster |
| 75. | sad | causing or showing sorrow |
| 76. | saddening | causing sadness |
| 77. | shattering | emotionally devastating or shocking |
| 78. | shocking | causing deep alarm or distress |
| 79. | somber | darkly serious and sad |
| 80. | sorrowful | full of sadness or grief |
| 81. | soul-crushing | emotionally devastating and bleak |
| 82. | star-crossed | doomed by bad luck |
| 83. | tear-jerking | making people cry |
| 84. | terminal | ending fatally or disastrously |
| 85. | terrible | very bad or distressing |
| 86. | tormented | suffering severe mental pain |
| 87. | tragical | having tragic qualities |
| 88. | unbearable | too painful to endure |
| 89. | undone | emotionally ruined or overwhelmed |
| 90. | unendurable | not able to be endured |
| 91. | unfortunate | marked by bad luck or sorrow |
| 92. | unhappy | marked by sadness or misfortune |
| 93. | unspeakable | too awful to describe |
| 94. | upsetting | causing sadness or emotional distress |
| 95. | woe-filled | full of sorrow or misery |
| 96. | woe-stricken | struck by deep sorrow |
| 97. | woebegone | showing great sorrow |
| 98. | woeful | marked by sorrow or misery |
| 99. | wrecked | badly damaged or devastated |
| 100. | wretched | very unhappy or miserable |