One of the main challenges undermining the characters’ efforts to satisfy The Necessity of Human Connection is their struggle with their own mental health. Death is increasingly present in the lives of the characters, especially as they age. Generational trauma haunts their relationships with their children and the lives of the children themselves. The Trials of Grief and Mental Illness are ever present, and the novel is oriented around exploring how those trials shape the perspectives and actions of its flawed characters.

The nature of the characters’ grief and mental illness often remains convoluted and shrouded in darkness, and the characters feel largely at its mercy. Olive Kitteridge, as her husband observes, “had a darkness that seemed to stand beside her like an acquaintance that would not go away” (6). Olive herself experiences this darkness as a sort of toxin that can flood her body with shocking speed. When Olive overhears her son’s first wife refer to her questionable parenting, “something stunned and fat and black moves through her” (70). Imagining a response to the woman, Olive tries to explain that “deep down there is a thing inside me, and sometimes it swells up like the head of a squid and shoots blackness through me” (71).