In this article, we address two distinct, but interrelated aspects of “skillful means” that can inform compassion training: 1) the historical precedent and need for adapting meditation practices to meet new cultural contexts, and 2) the need to express compassion flexibly in ways that creatively meet the specific contexts and needs of particular persons and situations. We first discuss ways that the doctrine of skillful means was employed by Buddhists to rationalize the repeated adaptation of Buddhist teachings to meet the culturally situated mentalities and needs of diverse Asian peoples. Then, in continuity with that history of Buddhist adaptation, we explore how theories from modern psychological science, such as attachment theory, can be newly drawn upon to support adaptation of Buddhist compassion training for application in modern cultures. Finally, we draw on theories from cognitive science, namely situated conceptualization, that provide a tractable framework for understanding skillful compassion as embodied emptiness—involving the relaxation of pattern completion mechanisms, which helps open up greater discernment and presence to others, so that care and compassion can be more unrestricted, creative, and directly responsive to the person and situation at hand.