1. (n.) Extreme pain, either of body or mind; excruciating distress.

2. (v. t.) To distress with extreme pain or grief.

ache aching heart afflict affliction aggrieve agonize agony agony of mind ail angst anxiety atrocious pain bale barb the dart bitterness blanch bleed bleeding heart blench boredom break down bring to tears broken heart bruise care carking care cheerlessness crucifixion crush crushing cut cut up depression depth of misery desolate desolation despair discomfort discomposure discontent dislike displeasure disquiet dissatisfaction distress disturb dole draw tears dread dullness embitter emptiness ennui excruciation existential woe extremity feel pain feel the pangs flatness go hard with grief grieve grimace grimness have a misery heartache heartbreak heartfelt grief heartgrief heavy heart hurt hurt the feelings infelicity inquietude inundate joylessness lack of pleasure lamentation languishment malaise martyrdom martyrization melancholia melancholy misery nausea nongratification nonsatisfaction oppress overwhelm pain painfulness pang pierce pining pound prick prostrate prostration rack regret rue sadness savorlessness shoot shrink smart sorrow sorrowing spleen stab staleness sting suffer suffer anguish suffering suicidal despair tastelessness tediousness tedium thrill throb tingle torment torture trouble twinge twist the knife twitch uncomfortableness unease uneasiness unhappiness unpleasure unsatisfaction upset vexation of spirit wince woe worry wound wretchedness writhe