60 entries under pessimistic topic. ×

10
pointless(adjective, stupid, dry, idle, useless)
9
bad(adjective, person, unhappy, gloomy, mood)
9
unfortunate(adjective, dull, bad, sad, unhappy)
8
unhappy(noun, adjective, upset, person, dull)
8
vain(adjective, sad, stupid, idle, useless)
8
helpless(adjective, sad, unhappy, miserable, useless)
7
impracticable(adjective, stupid, unreasonable, useless, trivial)
7
unavailing(adjective, weak, stupid, dry, idle)
7
woebegone(adjective, person, low, sad, unhappy)
7
cynical(noun, adjective, upset, sad, unhappy)
6
downbeat(adjective, person, feelings, uncertain, mood)
6
fatal(adjective, futile)
6
gone(adjective, informal, hopelessness, futile)
6
negative(noun, adjective, feelings, gloomy, uncertain)
5
discouraging(adjective, dull, sad, gloomy, miserable)
5
irredeemable(adjective, futile)
4
sinister(adjective, appearance, obscure, sad, dark)
4
tragic(adjective, sad, unhappy, gloomy, miserable)
4
defeatist(noun, adjective, feelings, gloomy, uncertain)
4
depressing(adjective, person, dull, obscure, sad)
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APASmart Define. (2016). hopeless thesaurus. Retrieved September 29, 2026, from https://smartdefine.org/hopeless/thesaurus/synonyms
ChicagoSmart Define. 2016. "hopeless thesaurus" https://smartdefine.org/hopeless/thesaurus/synonyms (accessed September 29, 2026).
HarvardSmart Define 2016, hopeless thesaurus, Smart Define, viewed 29 September, 2026, <https://smartdefine.org/hopeless/thesaurus/synonyms>.
MLASmart Define. "hopeless thesaurus" 24 March 2016. Web. 29 September 2026. <https://smartdefine.org/hopeless/thesaurus/synonyms>