This dissertation examines the relationship between compassion and alienation in contemporary Japan. That relationship is poignantly expressed in the experience of religious professionals working to "get close to the hearts of others." For those professionals, as for many scholars, sharing suffering is meant to overcome isolation in a society characterized by suicide, economic stagnation, and an aging population. However, after twenty-four months of intensive fieldwork with religious people working to provide "care for the heart" in order to overcome the anomie and alienation that plague contemporary Japan, I have found that sharing suffering hurts on multiple scales. Hearing stories from disaster victims exhausts my informants. Working to empathize with the suffering of others ties compassionate workers to depopulated and aging areas, making it difficult to find marriage partners or friends, and my informants' religious organizations are strained as they bear the financial costs of this work without proselytizing. In this dissertation, then, I argue that the pain of sharing suffering isolates compassionate workers and exhausts the forms of belonging, such as religious organizations, that support them. Using the examples of a new religion working to maintain community, a training program for interfaith chaplains working with people facing death, and a Christian volunteer center in a city devastated by the 2011 tsunami in Tohoku, Japan, I argue that compassion spreads the pain of social suffering while breaking down non- liberal forms of belonging, thus ironically creating an alienated society of isolated individuals.