Synonyms for Grief:

n.

be unsuccessful, fail, have trouble, suffer, be harmed. happy. adversity (noun)
poverty, trouble, bad luck, contretemps, ordeal, dolor, poorness, curse, catastrophe, tribulation, disaster, blight, misfortune, burden, hard times, trial, destitution, calamity, misadventure, peril, adversity, hardship, difficulty, rainy day, hard luck, woe, mishap, casualty, tragedy, bane.
cognition (noun)
sorrow.
dejection (noun)
despondency.
depression (noun)
unhappiness.
grief (noun)
heartbreak, heartache, sorrow, brokenheartedness.
lamentation (noun)
ululation, melancholy, plaintiveness, dolefulness, woefulness, mournfulness.
loss (noun)
bereavement.
mental suffering (noun)
sorrow, tribulation, desolation, misery, remorse, discomfort, dole, wretchedness, malaise, agony, mortification, despair, disquiet, heartbreak, gloom, trial, mournfulness, vexation, harassment, affliction, despondency, depression, trouble, lamentation, dolor, rue, pain, distress, unhappiness, bereavement, regret, anguish, worry, woe, torture, heartache, melancholy.
pain (noun)
bite, smarting, sting, irritation, rack, stitch, pain, misery, gripe, distress, wrench, affliction, torture, Back Ache, agony, throe, throb, stab, headache, ache, malaise, injury, crick, painfulness, infliction, discomfort, wound, chafing, torment, inflammation, cramp, pang, earache, spasm, hurt, sore, burn, bruise, suffering, Migraine, anguish.
regret (noun)
lamentation, qualm, sorrow, repentance, rue, heartache, remorse, contriteness, regret, penitence, shame, contrition, sorriness.

Other synonyms:

disappointment. depression, gloom. smart. misery
wretchedness.
sorrow
unhappiness.

Usage examples for grief

  1. " Your grief does you honour, Mrs. Duveen," he said. – The Orchard of Tears by Sax Rohmer
  2. So wild was her grief that she hardly knew what she was doing, and, after the play was over, she could not have told how she managed to get through it. – A Peep Behind the Scenes by Mrs. O. F. Walton
  3. For, being moods, they are unintelligble, and the man who tries to solve them usually comes to grief – A Romance of Wastdale by A. E. W. (Alfred Edward Woodley) Mason