While contemplative approaches have recently garnered much attention in different areas of transformative education, the interpersonal and relational aspects of contemplative training have received less scrutiny. This article examines the relational dynamics involved in contemplative education from a Lacanian viewpoint. The concept of transference is used to unpack the fantasies, desires, and errors involved in contemplation, a process aimed at deep existential realization. Transcripts of Zen Buddhist koan training from Philip Kapleau's classic book "The Three Pillars of Zen" are used as a case in point.