“The living human web” as the subject matter in pastoral theology arose twenty-five years ago in the context of the western individualistic society in which its previous counterpart “the living human document” had appeared about seven decades before. The metaphor captures ideas on the wider cultural and political contexts where pastoral care is located, especially in the hope of responding to the challenge of political and social injustice. Psychology in the United States appealed in the earlier years of pastoral care because of its deep respect for personal experience while it contributed to the disillusionment of academic theology in pastoral theology. The previous metaphor of the living human document depended heavily on the vivid clinical cases; in turn, the living human web that Miller-McLemore coined in the early 1990s was intended to capture “context, collaboration, and diversity” beyond individual counseling sessions. Underneath the shift of the paradigms, three trends can be identified as contributing factors: interest in congregational studies; a call for a new public theology; and the rise of liberation movements. With the advent of the new metaphor in pastoral care, the definition of genuine care has been changed as requiring an understanding of social sciences such as economics and political sciences as tools of interpretation. The meaning of the living human web has continued to develop until the day and there are four different emphases worth noting: political/liberationist, ecological/contextual, congregational, and educational/ministerial. Regardless of changing of metaphors, however, empathy that matters always in pastoral care is to be sustained by giving voice to the silenced and oppressed by others in culture.