List of 426 Sets of Synonyms - How they Differ - Total of 2307 Words - 319

SYNONYMS: regret, sorrow, grief, anguish, woe, heartache, heartbreak.
All of these nouns denote mental distress.

Regret has the broadest range, from mere disappointment to a painful sense of loss, dissatisfaction, self-reproach, or longing, as over something lost, gone, done, or left undone: . She looked back with regret on the pain she had caused her family.
Sorrow connotes sadness caused by misfortune, affliction, or loss; it can also imply contrition: It is to my sorrow that I did not apologize.
Grief is deep, acute personal sorrow, as that arising from irreplaceable loss: He felt grief over her loss.
Anguish implies agonizing, excruciating mental pain: I pray that our heavenly Father may assuage the anguish of your bereavement.
Woe is intense, often prolonged wretchedness or misery: Woe to those who treat your false.
Heartache most often applies to sustained private sorrow: The child's problems are a source of untold heartache.
Heartbreak is overwhelming grief: Better a little chiding than a great deal of heartbreak.