In this paper, we will describe the real and imaginary aspects of online therapies, explored through ongoing clinical experiences and via a questionnaire completed by a sample of clients who agreed to take advantage of the online setting. The research included participants completing a self-evaluation questionnaire using a Likert scale, which explores participants’ emotional experiences of online therapy and how it compares to traditional, in-person formats. When forming the questions, we tried to bring out the benefits and positive aspects of this digital practice. The unique environment created by online therapy has its own specific characteristics. The loss of the traditional “therapy room” is compensated by the discovery of new aspects of the client’s life that contribute to the therapeutic encounter, such as getting a direct view of the patient’s home and personal environment. In this new setting, unexpected stimuli and resources emerge that can support the therapeutic process. The real and imaginary elements of the online setting allow therapists to capture information about a client’s personality, the way the individual functions, and their interpersonal system of reference. By using as a reading grid the theoretical Intersystemic Articulation Model (M.A.I. [Italian acronym for Modello di Articolazione Intersistemica, elaborated and used in the Institute of Relational Psychotherapy (I.P.R. ) in Naples, Italy.]), we illustrate through clinical cases how both the real and imaginary aspects of online therapy give the client an exclusive opportunity for reflection and change, both in their intrapsychic world and interpersonal relationships.