Play is the context for acquiring social skills. While it is logical to suspect that the difficulties associated with ADHD would affect play, there is surprisingly little work in that area. Further, there is almost no previous research describing the playmates of children with ADHD. This study involved children with ADHD (n = 112) playing with a usual playmate (n = 112), and pairs of age-, ethnicity-, and sex-matched children (n = 126) playing together. In this paper, the authors interpret the data from the perspective of the playmates. The overall finding was that the play behavior of the playmates closely resembled that of the children with ADHD; it was characterized by low levels of empathy. A primary purpose of this paper is to explore possible explanations for this surprising finding. Two possible explanations are explored. First, children with ADHD are demanding playmates so that children who play with them mirror their negative behaviors. Second, although the playmates did not have ADHD, their play behaviors might reflect the known risk of negative behaviors reported amongst siblings and peers of children with ADHD. Evidence to support both explanations is presented and new lines of research are proposed to examine each possibility.