This study aims to assess whether children have measurably different relationships with some of the familiar adults in their everyday world. Assessment is made by observing preschool children in a conventional park playground, and evaluating whether their activities and social behaviour differ depending on the caretaker type/s accompanying them. The study is in three parts. The first is an empirical validation of the research venue. Since playgrounds are rarely used in developmental research, it is important to establish that the patterns of behaviour observed there are generalisable. The second part is a comparison of children accompanied by either mother, father, grandmother, nanny, or peer's mother. All 5 caretaker types were found to exert some unique influences, although similarities outweighed differences. The third part compares the effect of a single caretaker accompanying a child with the effect of two caretakers. This allows for assessments of the robustness of caretaker influences. Caretaker effects were found to be dynamic, with two caretakers having an effect which could not be predicted from their effects when alone with a child. There is also evidence of some caretakers having a more dominant effect on children's behaviour than others. It is concluded that caretaker roles provide consistent predictors of children's activity and social behaviour although roles are probably only one of a number of salient factors in determining the effect of different familiar adults on children.<p