Given that one of the major goals of the practice of Philosophy for Children (P4C) is the development of critical thinking skills (Sharp 1987/2018, pp. 4 6), an urgent question that emerged for one of the authors, who is of Chinese Heritage and a novice practitioner at a P4C summer camp (thinkingplayground.org), was whether this emphasis on critical thinking might make this practice incompatible with the fabric of Chinese culture. Filial piety (孝), which requires respect for one’s parents, elders, and ancestors is considered an important virtue in Asian culture, as is the preservation of harmony. But if one of the goals of P4C is to teach youngsters to courageously pursue reasoned dialogue, does this not set-up young Asians for serious conflict when they come face-to-face with positions that are articulated by elders, but which are ones to which they are diametrically opposed; a racist grandmother, for instance, or an uncle who insists that those at the Tiananmen Square uprising were nothing but hooligan’s. It is this question that we will explore in this presentation. In the process, we will come to the conclusion that, when positions seem irreconcilable, rather than continuing to pursue rigorous critical interchange that may do little other than escalate insult, the facilitator, rather, ought to move toward creating a deeper understanding of each position juxtaposed against its opposing view (a process that we refer to as ‘collaborative caring’), so as to produce side-by-side understanding, knowing that communal bonds have been maintained and, hence, that the opportunity for genuine reasoned collaborative inquiry on other issues and at future times remains open.