The present research looks into Paul Auster’s intriguing novel Oracle Night and initiates a metaphorical journey deep inside the architectural world of the postmodern self of his protagonist, Sidney Orr. Employing the “Virtual Fictional/ Factual Positioning” (VFP) theoretical framework, this article relates the experience of uncertainty as a central mode in the postmodern self and aims to establish whether Orr develops a dialogical self which, according to Hubert Hermans’ Dialogical Self Theory (DST), functions as a more developed self in the present era of globalization and cross-cultural movements. The findings indicate that Orr’s dialogical attempt is having positive affects which, in the end, are beneficial for the psychological health of his whole self-system.