Bless your heart (Wikipedia) “Bless your heart” is a phrase common to the Southern United States. The phrase has multiple meanings and is used to express genuine sympathy but sometimes as an insult that conveys condescension, derision, or contempt. It may also be spoken as a precursor to an insult to mitigate its severity. Meanings range from sincerity to exasperation, and are primarily imparted through context and tone. While common in the South, it is primarily used by individuals who wish to “be sweet” and do not wish to “act ugly.”