This article discusses how the intersection of grammatical gender and social gender, entwined in the core structure of language, can be analyzed to understand the dynamic status of selfhood. After reviewing a history of scholarship that demonstrates this claim, the discussion analyzes the language practices of transgender individuals in Japan, where transgender identity is currently understood in terms of sei-dōitsusei-shōgai (gender identity disorder). Based on fieldwork conducted between 2011 and 2017, the analysis reveals how individuals identifying with sei-dōitsusei-shōgai negotiate subject positions by manipulating the specific indexical meanings attached to grammatical structures.