This paper explores liminal sexual and gendered subjectivities and identities – in particular bisexuality, transgenderism, and intersexuality – with an attention to the intersections of race, culture, and class. It argues that the potential space of psychoanalysis should work to make room for forms of subjectivity that defy identity, and which often fall through the cracks of cultural intelligibility. It challenges psychoanalysts to tolerate ambiguity; to allow sexuality and gender to at once orient and disorient. It addresses the problem of identity itself, arguing that good psychoanalytic practice at once acknowledges the limitations of identity and accepts that its formation is critical to helping people make sense of their own complexity. It argues that queer theory should be a necessary part of psychoanalytic education. And finally, it offers numerous clinical examples, including an extended case study of a patient who struggles with the biological ambiguity of his sexed body and with the difficulty of finding the language to make sense of it.