How does a therapist respond to the presentation of an entirely new problem? HIV provides an interesting contemporary example of how therapists have come to define and redefine their role when working with chronically ill people, their families, and other professional caregivers. The problem associated with HIV infection, however, places therapists in double jeopardy Not only do they have to work with a disease, but also issues that arise in therapy sessions may be as personally relevant for the therapists as they are for the patients. These include issues about sex and sexuality, drug use, secrecy, death, loss, and personal risk taking, among others. A therapist's professionalism may not offer immunity or solace from these sometimes-painful issues. In this chapter we describe how, as therapists, we have applied systemic thinking to the development of a hospital-based therapy service and have attempted to respond to some of the complex psychological issues of patients and how this work has affected our relationship. It also describes how working in this field has changed our practice.