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In this paper, we will analyze the dynamic and relational drivers behind the choice to embark on a therapy via Skype. The fear of relationships could be the origin of this choice. Can Skype be a means by which the patient’s difficulties manifest themselves? We suggest that this is possible, and we will use the case of Matilde to show it. Matilde uses relationships to see herself, as she is unable to do this alone. She tries to find herself through others and the virtual world. She prefers to skip a session because the therapist’s webcam is not working rather than having the session without them seeing each other. Can we speculate that Matilde feels lost when she is in contact with herself without an other’s mediation? What are her fears? In this case, has Skype helped or slowed down the process? How would her borderline emptiness manifest itself in a traditional session? And what does it mean to live in the virtual world for a patient who tries to find herself through others? We will try to answer all of these questions, thinking about the functionality that technology has for some patients, for the therapist, and for the therapeutic process.