The transformation of suffering is at the heart of psychoanalytic and Buddhist practices. Our contemporary American dread of suffering goes against the grain of both methods and leaves the general public with little understanding of what suffering teaches. This article explores the similarities and differences between some psychoanalytic and Buddhist approaches to suffering, compassion, and transference. It also shows that a sophisticated theory of a relational self was developed as early as the 13th century by Zen master Dogen.