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Aesthetic play requires all participants to remain faithful to the intricacies and intensities of human experience. Teachers and students continually improvised within relations, adapting, building, and changing meaning. The indeterminate nature of aesthetic play assumes teaching/learning is complex and individual. All involved are oriented toward a sensitivity to the many relations present in teaching/ learning situations and deliberately seek out fragility’s presence in order to honor the existing complexity and individuality. Eisner explains, “What is mediated through thought are qualities, what is managed in process are qualities, and what terminates at the end is a qualitative whole.” Discerning these qualitative relationships entails a faith. The qualitative interdependence depends on faith as a catalyst. This is faith understood as being in touch with context, finding accordance with lived experience. Such accordance with lived experience takes the form of continuous dialogues between self and other. These dialogues of faith ask participants to venture into the unknown with an audacity and tentativeness. Audacity is required to place value on entering into such dialogues of faith. Belief takes up purpose as something to be worked toward, rather than something that is necessarily present from the beginning. Tentativeness refers to the exposed, uncertain nature such participation demands. Commitment is required, grappling and questioning in the pursuit of meaning. Negotiating between audacity and tentativeness embraces these contraries as interactive and interconnected relationships. In this way, dialogues move back and forth, making a way in a constant exchange between self and situation. Jardine claims that the task of inquiry so conceived “is not to dispel this tension, but to live and speak from within it.” Harboring within aesthetic play is an integral fragility with particular assumptions, values, and beliefs about teaching and learning. These assumptions, values, and beliefs center on teaching as a call to respond to needs, desires, and interests of children. Faithfully responding to this call necessitates centering/living with fragility as a productive power.