Sentient robots, a science-fiction (SF) staple, have often been presented as threats to humanity. These dystopian imaginations reveal our fears about the rapidly evolving technological landscape. SF has also explored what it would be like if a human could fall in love with a robot. Typically, this takes the form of a man falling in love with a female AI, perhaps reflective of the societal dominance of heterosexual male perspective. With AI’s increasing popularity in what is already dubbed the digital age, along with a loneliness epidemic, it would be useful to investigate the relationship between these phenomena. Since media reflects contemporary fears and desires regarding AI and technology and helps shape perceptions of the future and our relationship with technology, this paper studies the film Her (2013) directed by Spike Jonze and the miniseries Maniac (2018), created by Patrick Somerville and Cary Joji Fukunaga. Specifically, this paper studies the isolation faced by the main human characters in the digital age, the presentation of the AI and how they facilitate connection between the human characters and help them heal from past traumas. Overall, they vividly depict modern isolation, and how technology simultaneously exacerbates and alleviates this loneliness, presenting a relatively hopeful vision of the future.