The Spiritual Exercises of Saint Ignatius of Loyola are one of the most important paths of spiritual deepening in the Christian tradition. Despite the fact that Saint Ignatius offers a detailed methodological description to live the experience, it is often approached by people who perform daily meditation practices close to Zen. In this paper, we analyze the possibilities of living the experience of Ignatian Exercises from the base of Zen meditation. Does it mean to distort the Exercises proposal or can it allow an even more profound experience? The study is preceded by an historical description of the encounter between Zen and the Society of Jesus, which pays special attention to the figure of two important Jesuits in this dialogue: the German Enomiya Lassalle and the Japanese Kadichi Kadowaki.