Children’s participation in cultural, everyday practices and social interactions involving math and money can contribute to the development of their knowledge and skills in these domains. Further work is needed to uncover what features of these activities, such as aspects of the conversations that may occur (e.g., number and money talk), facilitate and/or are shaped by children’s understanding of money concepts and skills. The present study examined the extent to which parents engaged in conversations about numbers and money with their four-year-old children during pretend grocery play and the relations to children’s math skills. We found that talk about price labeling and exchanging currency or goods occurred most frequently and that money and number talk were not significantly related to children’s broader math skills. However, parents’ money talk was positively associated with children’s money-related math skills, and this association was driven by the co-occurrence of talk about money and numbers. Our results suggest that parent-child conversations in familiar contexts such as grocery shopping provide rich opportunities to discuss culturally relevant practices surrounding money and practice math skills in the context of monetary exchanges. Thus, it is critical to consider how existing family practices and everyday contexts support children’s early math learning.