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What role does the real relationship play in psychoanalytic supervision? While the real relationship's role has long been and continues to be considered with regard to psychoanalysis, it has received virtually no attention in the supervision literature. In this paper, using Horney's construct of the real self as conceptual anchor, I attempt to: (1) situate the real relationship squarely within the borders of the psychoanalytic supervision relationship; (2) examine the relevance of real relationship phenomena for the supervision experience; (3) provide some simple, ordinary yet meaningful examples of case dialogue that illustrate moments of real relationship in supervision; and (4) introduce the concept of real relationship rupture and consider its potential ramifications for and impact upon the supervisor-supervisee relationship. Just as ruptures can occur in the supervisory alliance, I propose that ruptures can also transpire in the supervisory real relationship, have the potential to reverberate throughout the entirety of the supervision experience, and depending upon how they are handled, can prove either constructive and relationally energizing and enlivening or enervating and eviscerating to supervision process and outcome.