The paper discusses Matthew Lipman's approach to inquiry as shaped and fashioned by John Dewey's model of scientific inquiry. Although Lipman's program adopted the major aspects of Dewey's pedagogy, at least two characteristics of that program stand out as radically different--his use of relatively free-form philosophical discussions to teach complex thinking, and his formulation and development of what he called a "community of inquiry" as a pedagogical setting for holding and sustaining such discussions. Here Lipman's Philosophy for Children program is seen as a framework for the design and performance of philosophical inquiry in the disciplines--something that he himself contemplated but never realized. In this paper I outline a few possible directions for opening spaces in school-based mathematical practices for philosophical deliberation in a community of inquiry, Lipman style. I argue that such an opening represents a potential expansion of students' mathematical experiences--a way of nurturing and integrating a sense of the philosophical perspectives of the discipline into the regular math class that is larger and more encompassing, and that promises to provide bridges for establishing richer and more meaningful connections and interactions with students' personal experience, with other disciplines, and with the broader culture; and thus a prime example of what Dewey called "educative experience."