Children with autism have atypical gaze behavior but it is unknown whether gaze differs during distinct types of reciprocal interactions. Typically developing children (N = 20) and children with autism (N = 20) (4–13 years) made similar amounts of eye contact with an examiner during a conversation. Surprisingly, there was minimal eye contact during interactive play in both groups. Gaze behavior was stable across 8 weeks in children with autism (N = 15). Lastly, gaze behavior during conversation but not play was associated with autism social affect severity scores (ADOS CSS SA) and the Social Responsiveness Scale (SRS-2). Together findings suggests that eye contact in typical and atypical development is influenced by subtle changes in context, which has implications for optimizing assessments of social communication skills.