Although there have been a few efforts to find useful intersections between the philosophy of John Dewey and feminist care ethics, there remains much to be explored and much to be gained. Dewey’s holistic and aesthetic approach to ethics provides an intriguing framework not only for enriching the contemporary notion of care ethics but also for how the habits of caring can be developed. Specifically, this essay focuses on Dewey’s notion of “dramatic rehearsal” within moral deliberative processes as fostering a caring imagination. Moreover, infusing an embodied dimension to Dewey’s concept of dramatic rehearsal suggests that rich experiences of character acting, also referred to as “method acting,” can exercise our empathetic and imaginative capacities. If dramatic embodiment is viewed as a potent method of empathy development, the implications for contemporary approaches to “moral education” are significant. Furthermore, in a world where communications, technology, and information demands have sped up decision making, Deweyan deliberative processes remind us that the complexity of caring requires longer temporal horizons. I begin with a brief discussion of the congruence between Dewey’s ethics and care prior to addressing the implications of dramatic rehearsal.