The study of African American English (AAE) has been historically focused on the dialectal variations of adolescent and adult speakers. More recent investigations of dialect used by very young AAE speakers were undertaken with the goal of describing the language produced by early elementary and preschool-aged children. One important outcome of these studies is increased attention to the importance of considering the impact of developmental influences in our characterizations of dialect use. In this study we explore the differences between primary caregivers and their young children in dialect use across generations by directly examining the dialectal variations apparent during play interactions between primary caregivers and their young children. We conclude that there is indeed evidence in these interactions of differences between the child and caregiver in the structure and use of individual AAE features. Another conclusion is that there are many similarities in the distribution of AAE between these older and younger interactants, highlighting not only their kinship ties but also their membership in the same linguistic community.