This chapter contributes to the ongoing debate about how people can understand transsexuality. Transsexuality remains controversial within the psychoanalytic and public consciousness. All too often pathologized within psychoanalysis and at times heavily politicized in the feminist and queer literature, clinical and theoretical discussions about transsexuality seem to evoke rigid, binary thinking and positions. The chapter contextualizes the struggle some transsexuals convey within a necessarily speculative developmental framework rooted in object relations and attachment theories. This developmental account is a hypothetical formulation focusing in on a particular dynamic feature of the transsexual experience, namely that of 'being seen', of being taken in visually and mentally by the other in a state of incongruity. The chapter also illustrates the hypothesis through a qualitative study involving interviews with eight transsexual individuals and through a five-year-long, once-weekly psychoanalytic psychotherapy with a Male to Female (MtF) psychoanalytic transsexual who underwent sex reassignment surgery (SRS) during this time.