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(We're restricting the list to terms we think are related to sorrow, and sorting by relevance.)
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1. regret
2. grief
3. grieve
4. sorry
5. pity
6. woe
7. mourning
8. sympathy
9. remorse
10. sorrowed
11. sorrowfulness
12. feel
13. pain
14. penitence
15. sorrowing
16. ruefulness
17. sadness
18. sorrower
19. lament
20. mourn
21. sorrowful
22. repent
23. rue
24. ruthful
25. sad
26. pathos
27. rueful
28. mournful
29. nepenthe
30. solace
31. attrition
32. bewail
33. doleful
34. heartache
35. heartbreak
36. heartbroken
37. lamentation
38. ruth
39. alack
40. commiserate
41. contriteness
42. contrition
43. dolor
44. dolorific
45. dolorous
46. heartbreaking
47. penance
48. plaintive
49. poignancy
50. self-pity
51. sore
52. wail
53. bemoan
54. bereavement
55. break
56. brokenheartedness
57. compassionate
58. compunction
59. condole with
60. condolence
61. dole
62. dolour
63. feel for
64. mournfulness
65. pathetic
66. plaint
67. poignance
68. regretful
69. ruthfulness
70. sympathize with
71. woeful
72. affected
73. afraid
74. alackaday
75. broken
76. brokenhearted
77. condolement
78. crocodile+tears
79. deplorable
80. depressing
81. depressive
82. dolourous
83. doole
84. dreariness
85. drearing
86. egrimony
87. egritude
88. good
89. grame
90. griefful
91. hard
92. heartgrief
93. heartsick
94. heavily
95. inarticulate
96. lachrymose
97. objection
98. ochone
99. routhe
100. saddening

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