The subject of this investigation is the correspondence between Wilhelm von Humboldt and Caroline von Dacheröden from 1787 to 1797. These are the years during which Humboldt's significant works on a theory of education were also written. By analyzing the characteristic self-statements, it becomes possible for the first time to trace the development of Humboldt's thoughts on education based on relational experiences using the sources. This shows that, in Humboldt's view, education as self-education cannot be understood as either monological or dialectical. Rather, the systematic center of his thought can be found in a dialogical middle, which, in loving encounters, serves as the driving force for the free interaction between self and world in various situations, enabling the release into individual selfhood.