This study presents a wide-ranging thesis on the basis of Gadamer’s hermeneutic philosophy. It is unusually multidisciplinary in approach and content including the domains of philosophy, art history and analytic psychotherapy. Its central thesis that mirrors and mirroring in the Western tradition of painting might be analogical to the varieties of ‘mirroring’ in the conversations between therapist and patient is interpreted as Gadamerian ‘fusion of horizons’ with an increase in understanding of both the pictures with mirrors and an analogical mirroring in a patient’s ‘text’ or tableau. Chapters devoted to the analogical scheme of interpretation, hermeneutic psychotherapy as ‘reflective participation’, mirroring in psychotherapy, mirrors and mirroring and their ontological value, hermeneutics of art and its particular hermeneutic conversation, and finally to mirrors in paintings culminate in a presentation of eight ‘double interpretations’. There the author takes the reader through clinical vignettes drawn from real published case-studies juxtaposed with paintings in which mirrors play an analogical role. The ‘double interpretations’ of various forms of Narcissistic Mirroring, Convex Mirroring, Anamorphic Mirroring, Medusan, Janusian and Athenean Mirroring are both empirically sound and strikingly original. The book is a creative example of object hermeneutics within the domain of Gadamerian philosophical hermeneutics.