This thesis explores the importance of tolerating and facilitating uncertainty as it is recognised by British Independent and Kfeinian psychoanalysis and contemporary British magic realist fiction. In Part I, I offer some theoretical investigations, arguing that postmodem and some psychoanalytic discourses, namely Lacanian psychostructuralism, remarkably fail to address the challenges facing subjects in late- twentieth, early twenty-first century consumer culture. In their inability to tolerate paradoxes and uncertainty, these discourses objectify the subject, through processes of depersonalisation, derealisation and desubjectification. To redress these problems, I offer the work of British psychoanalysts, specifically, that of D. W. Winnicott and Melanie Klein and her followers. These perspectives, I argue, better serve the contemporary subject by recognising the importance of paradox and helping develop facilitating environments for the realisation of creative experience. In Part II, I examine how the play of paradox is fostered in contemporary British magic realist fiction. Specifically, I look at how these narrative strategies attempt to move away from the vicissitudes of internal and external, certainty and uncertainty, reason and unreason, to negotiate a Winnicottian third, potential space. The conceptualisation of such a space, I believe, offers a place from which we can begin to dialogue, to draw ourselves out of the oppositional dialectics that have plagued the bourgeois subject. I believe that in the novels of writers such as Jeanette Winterson, Joanne Harris, John Fowles, John Murray and, most especially, Angela Carter, we can find alternatives to bourgeois conceptions of reason and rationality, alternatives that are not based on the paranoid-schizoid, primitive processes and depersonalisation necessitated by the Enlightenment and capitalism but instead upon, in Kleinian terms, depressive ambivalence and the recognition of whole-objects.