The family service work environment has been linked to the parent–worker relationship (relationship) for many years. However, there is still much to understand about how the working environment and these relationships are connected. This paper reports on a small-scale qualitative study exploring the story of eight relationships between parents and family workers in four rurally based family services in New South Wales (NSW), Australia. Hermeneutics provided a way of examining the dynamics of the relationships, as it enabled an in-depth exploration and interpretation of the participants’ perspectives of how they experienced and understood the relationship. It became apparent that the work environment is an important influence on the relationship. New insights that emerged include the important role that staff not directly involved in the relationship (such as other family workers, supervisors, and administration and other professional staff) may play in assisting relationships. They also include the way in which flexible service delivery options support parent feelings of comfort, readiness to change, reciprocity, a sense of ownership to the service and need for support outside of planned appointments (both during and after intervention has ceased). These all support the development and maintenance of such relationships.