Adolescents are the so-called “digital natives”: those born into a multiscreen society where experiences and life itself travel in the digital and virtual dimension. The contemporary world is going through a crisis of the narrative experience, because of the invasion of information. In this “liquid society” characterized by unpredictable changes and uncertainty, a paradigm of success based on beauty and perfectionism engenders a sense of inadequacy and denies the possibility of failure among younger generations. I first discuss these timely issues and their impact on adolescent development. I explore the potential role of psychoanalysis and Self Psychology in the critical transition from adolescence to adulthood, in reactivating the capacity to construct meaningful narratives about their lives and selves. In the second part, I present an explicative clinical vignette of a long analysis with a teenager for whom the world of social media was the only way into the world and became the only access to build a psychoanalytic relationship.