The authors investigate the personality traits of parents and children and their significant influence on the behavior of the other. Using the HEXACO model of personality, the authors examine the behavior of one hundred parent-child dyads on a playground to understand broader parent-child relationships. Their analyses reveal two opposed types of parental behavior (engaged parents versus unengaged parents) and child behavior (introverted cautious play versus autonomous energetic play) on the playground. The authors assert their study demonstrates that the personality traits of both parents and children as measured by the HEXACO model play a significant role in parental and child behaviors during play and in broader interactions.