In this paper, I aim to explore how an expansion in my sense of self resulting from explorations of meanings within a perceived transgression allowed for a long overdue expansion within my patient and fostered a development in our ability to reach and sustain an ever-deepening empathic connection. The primary thesis of this paper is that expansion within the analyst, though often unwelcome and painfully difficult, can illuminate greater complexity and radically redefine the idea of self and security in connection. Specifically, I focus on the transition between the false and the authentic self and ways in which that transition then enters clinical work. I also highlight the importance of continuing to focus on being present with the person before us, rather than minding the experience of intersubjectivity via theoretic constructions. I share relevant personal experiences and argue that a shift toward a more authentic self enhances the mutual and co-occurring process of expansion within a clinical dyad.