This article explores how late 18th-century German fairy tales negotiate the boundaries between imagination and social reality. Through close readings of selected narratives, it traces how the construction of “alternative realities” enables critical approaches that reflect the tensions of the Enlightenment period. Focusing on the works of Christoph Martin Wieland (1733-1813) and Christiane Benedikte Naubert (1752-1819), the analysis demonstrates that marvelous elements in these tales serve as vehicles for philosophical and social reflection. By creating fictional alternatives, these Enlightenment narratives invite readers to critically engage with contemporary discourses and reimagine existing social arrangements. The article thus shows how the genre participates in a productive dialectic between reason and imagination, offering “experimental” – in the sense of tentative or exploratory – models for social critique and transformation. Employing close reading methodology, this analysis identifies three distinct modes of what can be termed “social imagining”: reformist approaches that seek to improve existing structures, transformative visions that envision radical alternatives, and diagnostic perspectives that reveal fundamental incompatibilities between different orders of knowledge.