Given the current increases in the divorce rate and the number of single-parent families, the development of gender roles among children from single-parent families has received more and more attention. This study investigated how single parents influenced the formation of their children’s gender roles and family-related factors that benefited the development of gender roles in single-parent children. Through in-depth interviews with 24 pairs of parents and children from single-parent families, we investigated single parents’ and their children’s cognition on gender roles, parents’ parenting attitudes and behaviors during their children’s gender role development, and communication and interaction between parents and children. Results showed intergenerational consistency in the gender role concepts of parents and their children in single-parent families. However, the children’s gender role concepts were not completely and directly inherited from their parents, and could be affected by their subjective initiative. Additionally, single parenting did not necessarily negatively impact children’s gender role development, which depends on their parent’s parenting style. The study’s limitations are discussed, and future directions for in-depth research are suggested.