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

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