In the spring of 2011, we had the pleasure of participating in the 3rd Child and Youth Care (CYC) in Action Conference hosted by the School of Child and Youth Care at the University of Victoria, Victoria, British Columbia, Canada. We were invited by conference chairs Veronica Pacini-Ketchabaw and Jennifer White to participate in a roundtable discussion on the theme of “Conversations on Conversing in Child and Youth Care”. This theme was inspired in part by a recent posting to the CYC-Net listserv, which asked, “Why are people speaking about the field in ways I don’t understand?” Veronica and Jennifer sensed that this question – and the spirited, and at times fractious, discussion that it generated on the listserv – would provide an excellent platform for mutual learning, critique, and reflection. Thus they capitalized on the opportunity to extend a conversation that was already underway, and used the question as a departure point for our roundtable discussion. In this paper, four of us who participated in the roundtable continue this conversation, with each of us probing deeper and pushing further along the themes and ideas we discussed in Victoria. We are not so much responding to any particular questions here, but rather trying to articulate some of our critical reflections on the field as we each are experiencing it. We hope that readers might engage with some of ideas we present in this conversation on their own terms.