Somewhat frequently I receive email messages or other communications from parents asking me about how to introduce philosophy into their conversations with their children. The main advice I give people is to listen for the philosophical questions kids ask. I don't believe that bringing philosophical dialogue into your relationships with your children is about teaching them philosophy and looking for opportunities to do so (as we do with, say, teaching kids to read or learn math facts). It is really much more about listening and developing an ear for recognizing kids' philosophical questions.
As parents, we are often quick to answer our kids' questions. (That's a big part of the job of parenting, after all!) And I think that really that’s the most significant impediment to talking about philosophy with our children. Parents are often uncomfortable having conversations with our kids in which we don’t have the answers, and not very skilled at picking up on those questions for which an answer from us is not really what is sought.
You don’t need to have taken any philosophy classes to start these conversations with your children. We all have philosophical questions. Who am I? Why is there something rather than nothing? What does it mean to live a good life? Why am I alive? What is time? And kids have these questions too. In my experience, when you open the door to a discussion about questions like this with your child, he will be eager to explore them with you.
Your child might ask, for example, “Why are people so mean?” Instead of talking about the reasons you think people can be mean, whatever they are, you might instead respond by saying, “What were you thinking about when you asked that?” or “Why do you think people are mean?” or “Do you think some people are mean people, or do they just do mean things? Why?” Now it might be that in this case, what your child really does want is an explanation from you about why some of the kids at school are picking on her. But maybe not.
Being open to picking up on when a question might be philosophical creates the possibility of talking about these larger, fundamental questions. It can add a new dimension to your relationship with your child to examine together questions for which neither of you have the answers, questions that continue to be profoundly mysterious. In these kinds of conversations you can inquire together in a way that allows for a kind of equal give-and-take that is not present in most aspects of the parent-child relationship, deepening your relationships with your children. I have found that years of these kinds of discussions with my own children, now all teenagers, have really helped to develop a strong foundation for what these days are often more personally challenging conversations.