Fiction has explored the potential for artificial intelligence to fulfil a huge range of hopes and dreams. These include hopes for intimate relations stripped of the complexity and jeopardy associated with interactions with other humans. This chapter examines three categories of intimate human-machine relationship: as friend, as family member, and as lover. Drawing on examples from science fiction literature and film (ranging from the stories of Bradbury and Asimov to television series such as Westworld and Real Humans), this chapter shows that imaginative accounts have long recognised the tensions inherent in emotional relations between humans and AI. The chapter highlights three contradictions in particular. First, alienation from the machine: the artificiality of these machines constantly threatens to awaken feelings of unease, even revulsion—and the more human-like they become, the greater this risk. Second, alienation from other humans: inasmuch as the machines succeed in their purpose, they risk alienating us from each other, and undermining the social fabric of which they were intended to be part. Third, abandonment: the more humanlike or even superhuman these machines become, the more they bring with them the kind of complexities, demands and risks that plague human relationships. In conclusion, the chapter points to how speculative fiction has revealed the underlying tension in wishing for something fully human or even superhuman, yet simultaneously partial and subhuman.