Recent developments in public debate, health policy, and research on nontraditional families have brought gay-parent families, especially gay fathers, into the cultural and political spotlight. Existing research and literature on LGBT families and gay fatherhood have emphasized relationship dynamics within the families but there are gaps in the literature regarding the health and well-being of these families, specifically as it relates to health insurance. Using symbolic interactionism, life course theory, and grounded theory methodology, I conducted a qualitative pilot study to investigate gay fathers' health insurance experiences. I collected responses from 10 White, gay fathers across the United States and asked questions about access to health insurance, the process of providing insurance for their families, access and use of community resources, and unique factors of their health insurance story. This research adds to the same-sex parent knowledge based by (a) gaining an understanding of the family decisions gay fathers make around health insurance, (b) identifying obstacles and subsequent solutions to health insurance problems, (c) discussing issues of disclosure and outness in gay father families, and (d) uncovering continued gender associations with the division of labor. This study has more broad implications for theoretical concepts like intersectionality and agency, but also provides insights into policy inequalities that continue in the United States.