This paper describes the author’s work with three transgender and/or gender expansive patients. The treatments took place at various times over the past twenty years and are presented chronologically. The author, a cisgender analyst, shows how her thinking and her interactions with her patients have changed. In a sense, the analyst is also transitioning as her thoughts and feelings about her gender expansive patients shift. The importance of moving outside of traditional ways of thinking about gender is emphasized, as is the danger of seeking linear, formulaic answers to why a gender-variant patient does not feel at home in their body.