This paper discusses the Scottish philosophical roots of W. Ronald D. Fairbairn's theory of object relations and traces their influence on his subsequent contribution to psychoanalytic thinking and practice. It begins with a short and relevant account of a previously unpublished, and strangely mysterious meeting in Vienna between Freud and an earnest patient who had travelled across Europe to see him. The ensuing psychoanalytic themes that emerge from this uncanny encounter are developed in relation to Fairbairn's theory of the endopsychic structure of mind, and the importance of reality in the psychoanalytic relationship. A predominant thread running through the paper is the question of the roots of theory, whilst other themes of forgetting, repression, the doppelgänger, and the divided mind, are also considered. Fairbairn's adherence to critical realism is discussed in the context of Scottish culture as a significant ‘social object’. Examples of the phenomenon of the ‘Caledonian antisyzygy’ are taken from early Scottish scholasticism, and Scottish Gothic literature, and it is argued that Fairbairn's unique theory of object relations owes much to a cultural understanding of the divided mind.