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Aesthetic experiences reconcile human dualism between sensibility and reason and hence enables us to experience freedom of choice. This article investigates the interconnection of Schiller's Über die ästhetische Erziehung des Menschen and Adorno's Theorie der Halbbildung. Schiller foresaw the instrumental rationalism Adorno described as a consequence of Enlightenment and suggested that aesthetic education as a significant part of Bildung would be the protection against it. I interpret Schiller's philosophy as dialectical and him as a precursor of both critical theory and a hermeneutic/phenomenological understanding of art. This article analyzes aesthetic playfulness as a creation of emotional and rational experimental spaces that have an important impact on ethical and political formation.