Empathy is central to the interactions of occupational therapists who value personal dignity. Persons from various sectors of the behavioral sciences and the medical humanities have proposed that engagement with the arts can develop empathy, an assumption that prompted this inquiry. The observations of artists and art philosophers suggest that the assumption that art may develop empathy is grounded in the kindred natures of the two practices and in the actions that occur when a person engages with a work of art. The assumption that art may develop empathy is grounded in the kinship of the actions common to both practices: response, emotion, and connection. Artists and art philosophers’ observations of human practices have uncovered three rules of art that may dispose one toward empathy: reliance on bodily senses, use of metaphor, and occupation by virtual worlds. Analysis of art’s potential suggests that a person who would derive empathy from art must (a) use the senses to grasp feeling, (b) stretch the imagination to see a new perspective, and (c) invite an occupation that enhances understanding. Persons who hope to develop empathy must pursue an experience that evokes the fellow feeling that inspires it. Art can offer this experience.