As a former diplomat currently engaged in praxis-oriented research and teaching, I examine Böckenförde’s importance in the broad context of the debate on the future of Europe. First, I trace some of Böckenförde’s specific thoughts on the development of the European Union, notably concerning trends that impact on the shared “sense of belonging” that underpins deliberative democracy. Second, accepting Böckenförde’s crucial distinction between the granular provisions of the law and an underlying ethos or sense of direction, I argue that the Böckenförde paradox is strongly supported at the roots of our culture by ancient Greek political thought, in ways that can help us develop our thinking in new directions—involving Aristotelian conceptions of orientation, community (koinōnia), and discernment. Finally, I address the challenges currently facing the European Union, taking as my point of departure President Emmanuel Macron’s evocation of the “contribution which a living Europe can bring to civilisation.” The political thought of Ernst-Wolfgang Böckenförde, illuminated by conceptions of orientation, community, and discernment, can help to prepare us for a future intercultural dialogue in the service of peace.