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A recent article in the New York Times (Spencer, 2011) described a series of well-attended workshops on how to encourage children to play effectively with wooden blocks. At first glance, the idea of teaching children to play seems somewhat absurd. And yet, if we think about learning via play rather than learning to play, it is reasonable to ask how adults can encourage mathematical and verbal complexity in children’s games and activities. By looking closely at what parents and teachers say to children during play sessions, we can perhaps better understand the kind of language that supports intellectual development in the context of child-directed play. In this brief paper, I attempt to show how one teacher uses language to bring together learning and play in a math tutoring session. Specifically, I discuss an instance where the teacher finds a moment in a student’s self-directed game where it would be appropriate to introduce beginning math concepts.