Informed by a hermeneutic propensity, this arts-based autoethnography inquires into forms of social and participatory experience in contemporary art. A living art that uses people as the medium, this art operates in a cultural context stretching possibilities of objects, spaces, relations, discourses, and experiences in contemporary art. Often contested in contemporary discourse, I am interested in the ways in which these participatory art manifestations may be educative.Reaching a critical juncture through participatory art experience, I begin reexamining art, aesthetics, and the conditions for making meaning with art. Throughout this narrative inquiry, reflexively and hermeneutically begin to develop an emergently fluid range of aesthetic qualities for art conceived through a political aesthetic. I then mindfully attend to participatory practices by experiencing myriad artistic endeavors in London, New York City, the fifty-fifth Venice Biennale, and beyond.Engendering questions and confronting assumptions, while openly giving voice to my experiences verbally, poetically, and visually, I cautiously problematize the ways in which participatory practices in contemporary art relate to our living. I open and invoke a pedagogical exploration of the educative implications for these practices in art education and aesthetic education. In doing so, I revisit questions pertaining to participation, conditions for understanding, political aesthetics, aesthetic qualities, and education. The capacious possibilities of this inquiry become an invitation for us to critically negotiate potential significance of these contemporary art practices, as well as aesthetic qualities in our lives.