The paper draws on fictionalised composite case histories to explore themes in psychotherapeutic work with gender questioning and transgender young people. Gender and transgender are examined from psychoanalytic, cultural and philosophical perspectives. It is argued that the meaning of gender and transgender as an identity is rooted in unconscious processes and patterns of relationship. An ethical argument is made for a therapeutic stance, which remains curious about and receptive to complexity in therapeutic work with gender questioning young people and their families. The need for the therapist to be aware of their own blind spots in work with gender questioning young people is discussed.