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This paper offers a reading of Walter Benjamin’s autobiography, Berlin Childhood around 1900 (1932–1933) in relation with two early works: Conversation on Love (1913), and The Rainbow: A Conversation about Imagination (1915). Only recently have Benjamin studies begun to broaden our understanding of this philosopher’s formative period. In the 1910s, Benjamin was already laying the foundations of his philosophy, the “program” of his vocation as a critic centered on the Kantian concept of experience. The main objective of this paper is to show how this program was based on the articulation of the concept of fantasy with the notion of love. This fundamental articulation could be the starting point for the construction of the autobiographical subject in A Berlin Childhood around 1900 thanks to the transcendental constitution of its “I.” Consisting of a system of image production through which the original coloring of the lived experience is made transparent, the child’s imagination could find a model system of surprising affinities in the amorous union, with its specific alternation between love and hatred.