Children were essential to Byzantine strategies for survival and social advancement, as their reaching adulthood ensured family continuation, inheritance transmission, and the support of parents in old age. The death of an only child represented a significant obstacle to familial aspirations. This chapter examines the role of hope in future-oriented strategies centred on children and its emotional and social dimensions in Medieval Byzantium, by analysing two texts by Michael Psellos (1018–1078)—The Funeral Oration for his Daughter Styliane and The Court Memorandum regarding his adopted daughter’s engagement. It argues that hope serves a dual function: intensifying grief while also providing a mechanism for healing, enabling individuals to maintain a sense of meaning despite challenging circumstances.