Transgender individuals and families throw existing taxonomic classification systems of identity into perplexing disarray, illuminating sociolegal dilemmas long overdue for critical sociological inquiry. Using interview data collected from 50 cisgender women from across the United States and Canada, who detail 61 unique partnerships with transgender and transsexual men, this work considers the pragmatic choices and choice-making capacities of this social group as embedded within social systems, structures, and institutions. Proposing the analytic constructs of “normative resistance” and “inventive pragmatism” to situate (...) the interactional processes between agency and structure in the everyday lives of this understudied group of cisgender women, this work theorizes the liminal sociolegal status of an understudied family form. In so doing, it exposes the increasingly paradoxical consolidation and destabilization of sociolegal notions of identity, marriage, normativity, and parenthood—challenging, contributing to, and extending current theoretical and empirical understandings of agency and structure in twenty-first-century families. (shrink)