Children with autism spectrum disorder (ASD) demonstrate significant heterogeneity in their profiles of social interaction and stress responsivity. We evaluated behavior and stress response in 52 male children ages 8–12 in a naturalistic playground interaction paradigm involving a child with ASD, a typically developing peer, and a same-age confederate. Younger children in the ASD group engaged in 5.8 times more approach behavior and showed a lower cortisol response than their older peers. Those that verbally initiated with their peers also showed a higher cortisol response. Older children with ASD exhibited the highest stress responsivity, while younger children with ASD showed more willingness to approach others without apparent stress. Intervening early and often may contribute to improvements in social engagement in youth with ASD.