101 entries under painful topic. ×

85
unhappy(adjective, upset, dull, bad, hurt)
40
sad(adjective, awful, terrible, horrible, afraid)
38
miserable(adjective, upset, dull, mean, bad)
37
depressed(adjective, upset, dull, bad, hurt)
31
sorrowful(adjective, upset, dull, mean, bad)
29
mournful(adjective, upset, dull, mean, blue)
25
grievous(adjective, mean, poor, low, happy)
24
disconsolate(adjective, upset, dull, blue, sad)
21
doleful(adjective, bad, moving, low, happy)
21
dolorous(adjective, upset, dull, happy, sad)
18
forlorn(adjective, dull, bad, blue, low)
18
lugubrious(adjective, happy, sad, unhappy, dark)
16
desolate(adjective, dull, bad, blue, low)
12
dire(adjective, unpleasant, awful, terrible, miserable)
12
distressing(adjective, mean, moving, poor, low)
12
dreary(adjective, dull, bad, low, sad)
11
awful(adjective, sad, offensive, unhappy, unpleasant)
9
calamitous(adjective, sad, unhappy, unpleasant, awful)
9
cruel(adjective, sad, unhappy, unpleasant, awful)
9
grim(adjective, dull, sad, unhappy, dark)
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APASmart Define. (2015). woeful thesaurus. Retrieved September 30, 2026, from https://smartdefine.org/woeful/thesaurus/synonyms
ChicagoSmart Define. 2015. "woeful thesaurus" https://smartdefine.org/woeful/thesaurus/synonyms (accessed September 30, 2026).
HarvardSmart Define 2015, woeful thesaurus, Smart Define, viewed 30 September, 2026, <https://smartdefine.org/woeful/thesaurus/synonyms>.
MLASmart Define. "woeful thesaurus" 10 April 2015. Web. 30 September 2026. <https://smartdefine.org/woeful/thesaurus/synonyms>