Families and sports are spaces for “doing” and “undoing” gender. The author presents qualitative interviews with 30 American men who recall their parents’ involvement in the gender atypical sport of baton twirling. The author analyzes the data using “doing” and “undoing” gender as well as “hard” and “soft” essentialism frameworks. Mothers are often supportive of their sons’ twirling, contributing to “undoing” gender and relaxing “soft essentialism.” Fathers do not see baton twirling as a normative pathway to manhood or masculinity, thus reinforcing “hard essentialism.” Fathers often take on an absentee role in their sons’ twirling. In rare cases, fathers “do” gender by reformulating their sons’ twirling into a more recognizable sport. Findings consider how parents navigate gender when sons cross gendered boundaries in sports and the consequences for gender inequality.