One of the mysteries of the English language finally explained.
1‘she regarded him with doleful eyes’
mournful, woeful, sorrowful, sad, unhappy, depressed, dismal, gloomy, morose, melancholy, miserable, forlorn, wretched, woebegone, despondent, dejected, disconsolate, downcast, crestfallen, downhearted, heartbroken, heavy-hearted, despairing, desolate, grief-stricken
tearful, teary, lachrymose
informal blue, down, down in the mouth, down in the dumps, weepy
archaic heartsick, heartsore
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