Technological advances in the computer and communication fields (the internet, social networks, virtual realities,) have created a world in which most of our patients, especially pre-adolescents and adolescents, are immersed. In this paper we think about the meaning of ‘digital natives’ communication in the framework of the therapeutic relationship and the resulting countertransference. Interactions through technology, we argue, significantly reduce the difference between being together and being separate and can make it very difficult to experience a feeling of authentic intimacy or loss. Furthermore, exploring the world through the web does not provide children with the opportunity to ask questions and give voice to their doubts: it is a one-direction communication. These elements need to be considered in the therapeutic relationship with pre-adolescents and adolescents. In this paper we present three cases in which the world of internet enters into the sessions and we illustrate the countertransference this arouses and how it needs to be worked through.