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In this wide-ranging and generative conversation, Ann Pellegrini and Avgi Saketopoulou reflect on the origins of their collaboration and the theoretical, clinical, and political commitments that shaped their coauthored book Gender Without Identity. Tracing their distinct yet converging paths – from academic, activist, and clinical spaces – they explore how transness is often misunderstood, pathologized, or contained within psychoanalytic discourse, and argue instead for an expansive, ethically grounded psychoanalysis that embraces gender variability as fundamental rather than exceptional. Drawing on Laplanche, Ghent, Bromberg, and Glissant, among others, the discussion spans questions of surrender, libidinal life, intergenerational trauma, and the reorganization of theory itself under the pressure of gender. They challenge binaries between sexuality and gender, activism and analysis, clinical neutrality and sociopolitical complicity, making a case for theory as a living practice responsive to trans lives and the unconscious alike. They both offer not only insight into their thinking but also a model of interdisciplinary dialogue – one in which curiosity animates the work of rethinking psychoanalysis from the inside out. Rethinking psychoanalysis, not in spite of transness, but through it.