Many children with attention deficit hyperactivity disorder (ADHD) have serious social and peer difficulties that can lead to adverse outcomes in adolescence and adulthood. Play provides a natural context to explore those interactional problems. This study aimed to examine the similarities and differences in play behavior of children as having ADHD and typically developing children. Participants were children (aged 5 to 11 years) diagnosed as having ADHD (n = 112) and typically developing peers (n = 126) who were matched based on age, ethnicity, and gender. The Test of Playfulness (ToP) was used to measure play. Children with ADHD performed similarly to typically developing peers on ToP items that related most directly to the primary symptoms of ADHD but scored significantly lower on several ToP social items; however, they also scored higher on one difficult social item and no differently on two others, suggesting that the problems may be developmentally inappropriate lack of empathy rather than simply poor social skills.