Jason Taylor aims in this article to establish two related claims: first, that the features of games provide fertile grounds on which long term philosophical engagement can be fostered; and second, that the attitude of playfulness is a happy bedfellow for the attitude and dispositions that dialogical inquiry is designed to foster in both participants and facilitators. He hopes to show how the incorporation of play--"qua" games and "qua" the disposition of playfulness--into various activities, approaches, and iterations of the philosophy for children (P4C) promises to enrich the Communities of Philosophical Inquiry (CPI) experience. To the extent that this demonstration is plausible, it can be understood as an argument that games, play, and playfulness "should" be incorporated. To establish the article's arguments, he will look at some of the literature on games (specifically that literature discussing the importance of rules) and playfulness (specifically that literature that presents playfulness as "responsive openness") in an attempt to extract some features of those concepts which will help to theorize more carefully about the (admittedly anecdotal) insights drawn from experiences. He tries to draw both from the literature on the philosophy of sport, as well as the literature from the philosophy of education--including John Dewey's claims surrounding experiential learning and the "forked road of doubt," as well as Tim Sprod's more recent concerns about seeing the results of CPI dialogues applied to everyday life.