This paper takes up the clinical challenges of working with patients for whom the repetitive pursuit of intense, erotic relationships both expresses and conceals yearnings to be and belong. While sexual experiences can elicit core fantasies of transformation, awareness of the very otherness that offers such promise also threatens a fragile self and is thus negated. A detailed clinical account illuminates sexuality’s dense entanglement with experiences of coming alive and the knotted strands of character armor, sexual charge, developmental trauma, disintegrative anxieties, and concretized longings for physical touch that permeate eroticism in the space of breakdown. The author takes up how these unstable intersections contribute to patients’ and analysts’ fears and avoidance of engaging these entanglements in the analytic relationship with its inherent seductions and frustrations; at the same time, it’s through delving into and living through these overlaps that the basic issues of being and becoming can emerge.