The question posed by Friedrich Schleiermacher, “What, in fact, does the older generation want with the younger generation?” (Winkler 1998), which for the first time addressed intergenerational relations in the context of parenting, remains a contemporary and relevant question. Similarly, the inverse question—“What does the younger generation want with the older generation?” (Ecarius 1998)—addresses intergenerational relations and intergenerational relationships that organize coexistence within families and society. The relations between generations are no longer predetermined (Schönbohm 2008), the living conditions and experiences of younger people and their families are changing, and confrontations between generations (Müller-Salo 2022) are becoming apparent, leading to crises, disruptions, and generational divides. Both younger and older generations are equally confronted with socially relevant issues such as dealing with wars, climate and environmental policy, democracy, right-wing extremism, migration, and diversity, and they are called upon to take a stance on these issues in the debate on social transformation processes and future plans. In youth and family research, generational crises and conflicts serve as a starting point for examining how younger and older generations shape their relationships and how they address perceived conflicts and crises through dialogue. The family is one such setting in which relationships are established across generations and where both older and younger generations confront conflicts and crises arising from the aforementioned challenges. In this context, the present article relates the topic of generation to youth and family. The focus is on the generative dialogue between the younger and older generations within the family, in which both familial and societally shaped expectations of normality, as well as socially relevant issues and crises, are addressed.