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In his article “The Enigma of Ana: A Psychoanalytic Exploration of Pro-Anorexia Internet Forums,” Dr. Tom Wooldridge highlights the positive, transitional potential of cyber communities, specifically the pro-anorexia web culture, for otherwise isolated patients. In our discussion, we describe theoretical parallels between a self-psychological and relational orientation and Dr. Wooldridge’s perspective on eating disorders as well as the transitional experience that chat rooms on pro-anorexia websites can provide. Additionally, we raise concerns about his thesis, specifically, the dangerous addictive lure of the pro-anorexia sites that can flood users with anxiety-provoking images and tips for maintaining severe restriction. We suggest that these problematic dimensions, in addition to the features of boundlessness and disembodiment inherent in cyberspace, may negatively interact with and reinforce maladaptive disordered eating, poor reality testing, and dangerously omnipotent defenses. The authors suggest a comprehensive approach that honors the adaptive, transitional function of chat rooms while actively addressing the problematic and negatively reinforcing aspects of these websites in the ongoing treatment dialogue.