This book offers innovative and integrative psychological theorizing on the meaning of parasocial relationships, drawing on cutting-edge empirical insights and clinical observations. Uniquely, the book explores various digital spheres, ranging from online dating and social media to subscription platforms like OnlyFans and AI-driven chatbots, including ChatGPT, AI-companions, and therapy bots. It highlights their specific characteristics, overarching similarities, dynamic entanglements, potentials, and risks, and finally, their meaning for the social self. Through this lens, the book examines how individuals initiate and sustain relationships, how intimacy and sexuality are experienced online, and how these digital practices materialize in everyday life, impacting meaning-making and broader societal organizing.Finally, the book offers conceptual ideas on media and AI literacy, as well as psychological implications, relevant to social work and education, counselling and psychotherapeutic contexts, policymakers, and everyone involved online.