In this essay, I use findings from the methodology of historical approaches in pedagogy to apply methodological questions to didactics. Historical approaches to didactics have earned scarce attention, which causes significant problems in the absence of notions about how a researcher can appropriately connect present interests and past texts. By referring to the current debates in historiography and the history of ideas in Japan, the difficulties of bridging the gap between the presentness of interpreters and the historicity of past texts are revealed as a common issue for pedagogical studies. I then shift our focus to German pedagogy to provide evidence to reevaluate the hermeneutic tradition, which prepared and absorbed several methodologies from problematic historical contexts. I use context analysis to enhance the consciousness of the organizing relationship between the past and the present; between interpreters’ interests and historical texts. To examine the development of those historical approaches, I focus on the research history of classical figures in German pedagogy to understand the achievements and challenges of the historical review of theories. Through these examinations, I reconstruct the framework of historical approaches to bridge the gap between past and present, while mentioning remaining problems.