In this article, I examine loss, the vicissitudes of empathy, and the existential complexity of one's subjective life in relation to the lived experiences of others. I focus specifically on some observations I made about the dynamics of empathy and the experience of grief during a recent trip back to the island of Yap (Waqab), Federated States of Micronesia. In so doing, I argue for the significance of recognizing that empathy is rarely an all or nothing affair. Nor is it necessary that it be based on some set of homologous experiences shared between individuals. It is, instead, a process that is temporally arrayed, intersubjectively constituted, and culturally patterned. Even in the face of mutual misunderstanding, possibilities still exist for moments of empathetic insight to arise.