The study focused on cultural, contextual, and gender differences in children's peer talk. Same-sex dyads of Estonian (n = 38), Finnish (n = 38), and Swedish (n = 34) preschool age children were videotaped during unstructured and structured play settings. We found only one gender difference in children's talkativeness and in the use of regulatory speech: during free play, Swedish boys used more imperatives per directives than Swedish girls. At the same time there were significant cultural and contextual differences. Estonian children were most directive and Swedish children were least directive. Finnish children were less directive than Estonian children but more directive than Swedish children. It was concluded that cultural and contextual factors strongly influence the likelihood, extent, and nature of gender differences in peer talk.