In this dialogue, we ask whether it is possible that the war in Ukraine could have been avoided and, if so, in what ways. The first chapter is methodological. We consider nodal points of history in terms of counterfactuals and contrastive explanations. We agree that “why?” and “what explains?” questions are contrastive and must be defined in terms of contrast spaces, although we do not necessarily agree on how to formulate those questions in the context of Ukraine. What exactly are the historical moments and situations where acting differently would have been a real possibility and could have had a major impact? Can we distinguish between proximate or immediate and ultimate or underlying causes of war? In what ways is history layered? The way we pose questions is also related to various pragmatic concerns and our positioning in social relations, and both involve normative considerations, for example in terms of responsibility.