Synonyms of unhappy

1 Syllable
bleak, blue, low, hurt, down, grim
2 Syllables
damndest, bleeding, hapless, gaucher, tragic, dismal, downcast, heartsick, hurting, mournful, mirthless, teary, broody, jonah, woeful, dreary, cheerless, punker, downbeat, troubled, let-down, dragged, damned, wretched, bummed, ripped, destroyed, hard-time, tristful, forlorn, sorry, gloomy
3 Syllables
despondent, graceless, malcontent, long-faced, unpleasant, chapfallen, grief-stricken, disgusted, ungenial, ill-fated, damnedest, unlucky, depressed, heart-rending, saddened, aggrieved, crestfallen, defeatist, untoward, sorrowful, dysphoric, dejected
4 Syllables
saturnine, melancholy, heavy-hearted, unsatisfying, unfulfilling, disappointed, down-in-the-mouth, woebegone, oppressive, heavyhearted, unhopeful, dispirited, melancholic, tenebrific, disappointing, unsatisfied, miserable, regrettable
5 Syllables
infelicitous, disconsolate, unfortunate