Notions of dialogical inquiry and of the dialogical self have become increasingly influential in contemporary psychology in response to the limitations of the traditional view of monologically encapsulated and radically disengaged consciousness. Conceptions of self and inquiry as intrinsically embedded in and constituted by our shared life with others seem to do better justice to the richly interconnected character of contemporary life. At the same time, our highly interconnected global world has also tended to foster a flattening of cultural and inter-cultural horizons that undermines dialogical engagement in any deeply meaningful sense. What is needed is to enrich current conceptions of dialogue with an understanding of experiential and cultural depth. This paper seeks an understanding of the depth dimensions of dialogue through an engagement of dialogical self theory with Jungian dialogical thought. Critical to this engagement is to appreciate the expressive potential of Jungian dialogism beyond Jung’s theoretical claims about dialogue.