In interreligious dialogue, the contemplative encounter remains underexplored, yet it may prove essential for cross-religious engagement. The contemplative encounter goes beyond the cultivation of religious literacy and the flourishing of mutual understanding. Those of other traditions are enjoined as partners in the search for existential fulfilment and are approached as fonts of insight for theological reasoning and sources of valid spiritual wisdom. After briefly reviewing key Vatican documents on dialogue, I propose that there is both a created space and a need for a deeper dialogue of spirituality. Three themes reveal and reflect the possibilities of this encounter—a renewed intrareligious (that is, introspective) dialogue, a rediscovery of key symbolic portrayals of this space of dialogue, and an exploration of the dialogical and spiritual virtue of silence. In this paper, I portray some of the contours and hopes of a renewed praxis of contemplative encounter among traditions, and, particularly, in the life of the Catholic Church. Such a movement may prove invaluable to the development and growth of many areas of Catholic theology and vital for the life of the global church.