For many decades, pastoral caregiving was merely described in terms of psychological terminology. Although most helpful, caregiving implies more than merely counselling techniques and listening skills dealing mostly with the affective and cognitive dimension of our being human. Family, intergenerational, social and relational dynamics imply more than conversing, talking and verbalising. At stake, is the quality of relationships and the trustworthiness, legitimacy and authenticity of human encounters. It is argued that human encounters should be directed by justice, ethical sensitivity and an ethos of compassionate being-with the other. It implies a new understanding of time as being present in the mode of nurturing, forgiving, reconciling and unconditional embracing of even the other as resisting opponent. In order to establish mutual trust and confidence, timing in relational issues implies sharing, coexisting and reaching out to the woundedness of the other beyond social presuppositions and stigmatising prejudices. In this sense, encouraging encounters could be viewed as an indispensable link in theoretical and paradigmatic reflection on true dialogue as an essential feature of pastoral caregiving. It contributes to academic discourses in the discipline of clinical pastoral care as well as to the pastoral ministry. Its aim is the fostering of hope, comfort, healing and the resilient courage of bouncing back despite painful setbacks in life. To capture the core argument in encouraging encounters, we can use the words of Thomas Mann in his novel Joseph and his brothers: "The essence of life is presentness."