12
rueful(adjective, happy, sad, pain, sorrow)
11
awful(adjective, sad, offensive, unhappy, unpleasant)
11
execrable(adjective, awful, terrible, horrible, afraid)
10
heartsick(adjective, sad, unhappy, terrible, sorrowful)
10
piteous(adjective, mean, low, sad, pain)
10
very upset
9
calamitous(adjective, sad, unhappy, unpleasant, awful)
9
comfortless(adjective, dull, mean, bad, poor)
9
crestfallen(adjective, sad, unhappy, unpleasant, woe)
9
cruel(adjective, sad, unhappy, unpleasant, awful)
9
dispirited(adjective, bad, blue, low, sad)
9
downcast(adjective, bad, blue, low, sad)
9
dreadful(adjective, sad, awful, terrible, horrible)
9
flagrant(adjective, awful, terrible, strange, horrible)
9
glum(adjective, blue, low, sad, unhappy)
9
grieved(adjective, sad, sorrow, depression, woe)
9
grim(adjective, dull, sad, unhappy, dark)
9
morose(adjective, blue, sad, gloomy, melancholy)
9
odious(adjective, awful, terrible, horrible, painful)
9
tearful(adjective, upset, sad, sorrow, depression)
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APASmart Define. (2015). woeful thesaurus. Retrieved September 25, 2026, from https://smartdefine.org/woeful/thesaurus/synonyms
ChicagoSmart Define. 2015. "woeful thesaurus" https://smartdefine.org/woeful/thesaurus/synonyms (accessed September 25, 2026).
HarvardSmart Define 2015, woeful thesaurus, Smart Define, viewed 25 September, 2026, <https://smartdefine.org/woeful/thesaurus/synonyms>.
MLASmart Define. "woeful thesaurus" 10 April 2015. Web. 25 September 2026. <https://smartdefine.org/woeful/thesaurus/synonyms>