My intention here is to consider the ways in which cyberspace has come to intersect with psychoanalytic space. I will do so by considering how clinical exploration of our patients’ experiences with e-mail and other digital media resonates with evolving psychoanalytic accounts of self, subjectivity and relation. Concepts such as “enactment,” “multiplicity,” and “paradox” represent some of the diversity of psychoanalytic opinion on how the psychoanalytic exchange is best conceptualized. The digital revolution likewise challenges fundamental assumptions. The everyday immersion in cyberspace that is increasingly common for many of us deconstructs traditional beliefs about what is private and what is public. Foundational notions of “interiority and “depth”—so central to everyday clinical work—are transformed in digital environments in which multiple realities and identities appear to co-exist seamlessly as a function of the interlinked architecture of the Internet.