Hope and hopelessness are coexisting and powerful experiences in the human condition. The dynamics of hope and hopelessness within intimate relationships are complex, and individual and family experiences of hope and hopelessness are embedded within historical contexts and wider social processes. This article rests on a relational set of understandings about hope and hopelessness, and offers a dual exploration. It focuses first on the complexities of the patterns of hope and hopelessness within families, and then on the complexities of the therapist's relationship to hope and hopelessness and the family's experience. Orienting to the balance of hope in constellations of hope and hopelessness provides one compass point of therapeutic practice. Reflective practice enables the use of the therapist's involvement in the therapeutic relationship, and helps the therapist to witness the coexistence of hope and hopelessness in a way that nurtures hope and emotionally holds both hope and hopelessness.