7
tearful(adjective, bad, sad, sorrow, depression)
7
grieved(adjective, bad, sad, sorrow, depression)
6
joyless(adjective, sad, pain, sorrow, depression)
5
cheerless(adjective, blue, sad, pain, depression)
5
comfortless(adjective, sad, pain, sorrow, depression)
5
dejected(adjective, sad, sorrow, depression, woe)
5
depressed(adjective, blue, sad, depression, woe)
5
depressing(adjective, blue, sad, pain, depression)
5
grieving(adjective, sad, unhappy, miserable, regretful)
5
regrettable(adjective, happy, sad, sorrow, depression)
5
aggrieved(adjective, upset, cut, hurt, hit)
5
desolate(adjective, blue, sad, sorrow, depression)
5
soul-crushing
5
tragic(adjective, bad, sad, sorrow, depression)
5
wistful(adjective, sad, sorrow, depression, woe)
4
affecting(mean, low, sad, pain, miserable)
4
distressing(adjective, mean, low, sad, pain)
4
grief-stricken(adjective, sad, melancholy, sorrowful, mournful)
4
hurt(adjective, upset, sad, unhappy, gloomy)
4
dispirited(adjective, blue, sad, depression, woe)
11 years ago|10k views|share |citing 
APASmart Define. (2015). rueful thesaurus. Retrieved September 26, 2026, from https://smartdefine.org/rueful/thesaurus/synonyms
ChicagoSmart Define. 2015. "rueful thesaurus" https://smartdefine.org/rueful/thesaurus/synonyms (accessed September 26, 2026).
HarvardSmart Define 2015, rueful thesaurus, Smart Define, viewed 26 September, 2026, <https://smartdefine.org/rueful/thesaurus/synonyms>.
MLASmart Define. "rueful thesaurus" 13 April 2015. Web. 26 September 2026. <https://smartdefine.org/rueful/thesaurus/synonyms>