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This paper traces my personal experience of a missed opportunity with a patient as it reverberates within me across decades. I discover that my experience is transformed, in part by the process of writing, from dissociation to guilt, then to curiosity and regret. Regret is presented as a more complex emotion than guilt in that it is less characterized by self-reproach and reflects some measure of acceptance along with disappointment and sadness. Writings of Aron, Josephs, Searles, Slochower, Winnicott, and others are employed in the development of this theme.