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

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