Recent years have witnessed an increase in the number of academic studies on the impact of technological advancements on human life, including possible transformations and changes in human sexuality following the development of sex-related devices, such as sex robots. In this context, terms such as posthuman sexuality, digisexuality, and techno-sexuality have emerged, signaling possible new understandings of sexual, intimacy, and emotional practices. It is important to note that ancient history shows that humankind has for a long time been fascinated with their relationship to non-living things, mostly human-like figures, such as dolls. The Ningyo (人形, the Japanese term for doll) has a long history of usage, and has deep religious and animistic significance in the Japanese context—there are records of sexual use as early as the 18th century. With this context in mind, this paper focuses on three Japanese examples, aiming to shine a light on beyond-human relationships, which include a Japanese man’s marriage to a digital character, sex dolls, and communicative robots, from both a sexual and emotional perspective. In a new horizon of sexual and romantic possibilities, how will humans respond, and what can emerge from these interactions?