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ache to feel pity, compassion, or sadness. [1/4 definitions]
alack used to indicate dismay, sadness, or regret.
con dolore with grief or sadness; sorrowfully (used as a musical direction).
depressing causing or having the potential to cause sadness and pessimism.
disillusioned having lost or been stripped of one's hopes or illusions, often resulting in disappointment or sadness.
doleful full of sadness, sorrow, or melancholy. [1/2 definitions]
gloom a mood or atmosphere of sadness or melancholy. [1/5 definitions]
glum showing sadness or gloominess. [1/2 definitions]
heavy-hearted burdened by sadness; depressed; dejected; melancholy.
melancholy suffering from or tending to suffer from sadness, gloominess, or depression. [1/3 definitions]
mournful arousing feelings of sadness; depressing; gloomy. [1/2 definitions]
pathos a quality in life or art that evokes pity, sadness, or compassion. [1/2 definitions]
plaintive showing or expressing sadness or sorrow.
poignant deeply touching; arousing strong emotion, esp. sadness or sympathy; piercing; penetrating.
sadly in a manner that exhibits or expresses sadness. [1/2 definitions]
shadow a time or an instance of sadness or gloom. [1/12 definitions]
sorrow the suffering or distress resulting from an injury, loss, misfortune, or the like; grief; sadness. [1/4 definitions]
sympathy kind understanding and concern felt for others because they are having difficulty, suffering, or are experiencing sadness, grief, anger, or the like. [1/6 definitions]
wistful displaying or characterized by yearning or wishful sadness.