Abstract Empathy is considered a key component of chaplaincy care, but little is known about the daily practice of empathy and the empathy barriers that chaplains encounter. This study investigates the factors that encourage or discourage empathy and provides insight into what chaplains actually do to achieve empathy and to overcome empathy challenges. Semistructured interviews were used to collect data from twenty humanist chaplains in the Netherlands. A grounded theory approach was applied to analyze the data. The core concept of empathic flow emerged from the analysis. This refers to the stream of empathic experiences that arises within the relational, dynamic exchange between chaplain and client. Based on the analysis, three types of empathic flow were distinguished: (1) uncomplicated empathy, which flows smoothly and easily; (2) challenged empathy, which fluctuates between flow and temporal stagnation or disruption; and (3) failed empathy, in which the flow of empathy is blocked. Professional empathy emerged as a second core category from the interview data. This refers to those chaplains’ activities that aim to establish or enhance empathic flow, particularly in the face of challenges. Professional empathy relies on several underlying key components: critical self-reflection, self-care, professional standards, and the chaplain’s humanistic worldview and values. The qualitative analysis yielded 10 themes of professional empathy. Our findings suggest that empathy is a rich and complex practice to which both chaplain and client contribute. As professional caregivers, chaplains consider themselves ultimately responsible for establishing empathy and overcoming challenges.