Patients often come to treatment with difficulties in creating and forming romantic relationships. As therapists, we accompany them in this delicate and sometimes fraught process. Many patients turn to dating apps (e.g., “Tinder,” “OkCupid”) in order to try and find something truly meaningful to fulfill their lives. These platforms occupy their everyday lives, consuming their time and mental energy. The present article suggests that observing some of the unique qualities of interactions that take place in dating apps may provide a lens that reflects, emphasizes, and teaches us about human struggles of intersubjectivity, complexity, and sense of agency, which are at the core of psychoanalytic interest. Clinical examples illustrate these psychic aspects, as well as the way they may be processed in the therapeutic encounter.