I discuss the origins of the capacity to hope, its roots in the infant’s experience of a loving and secure relationship with their caregiver. The infant’s awareness of his or her own mental and emotional agency can gradually develop and so the capacity to channel desires and impulses, and to expect an attuned response. I suggest that the failure of this intersubjective developmental process gives rise to an enduring sense of hopelessness, an expectation that emotional needs and desires will never be met. The key role that play has in the development of hope is discussed from psychoanalytic and neuroscientific perspectives. The impact that a patient’s persistent hopelessness has for psychoanalytic psychotherapy practice is explored, its function as a defence against any new, spontaneous relational experience which might activate trust and hope. Internal and external change and transference dependence are resisted as the patient fears becoming vulnerable to being abandoned or rejected by the analyst. I explore some socio-political aspects of hope and hopelessness, such as the belief that people deserve their success in society and the self-blame, shame and hopelessness that result from an experience of economic or social failure. I discuss the possibility that hope in human relationship and in our humanity can survive in the face of overwhelming catastrophe.