This chapter examines how contemporary television and film—particularly television series Mad Men and the films Her and Ex Machina—stage the interplay of nostalgia, fantasy, and desire within the context of gender, technology, and capitalism. Drawing on psychoanalytic theory (especially Lacan’s concepts of sexuation and the gaze), the chapter analyzes how media representations of the past and near future both reflect and complicate cultural anxieties about masculinity, femininity, and authenticity. It argues that these narratives use distance (temporal, technological, and psychological) to sustain fantasies of completeness and to commodify longing in order to mask the impossibility of fully resolving desire. The chapter concludes that the pleasure and frustration found in these stories mirror the structures of repetition and failure that underpin both masculine sexuation and broader social dynamics.