In this essay I have attempted to explore the lure of humans becoming machine-like, as well as the terrifying aspects of this evolving intimacy. The relief from loneliness, the escape from one’s own stressful mind and emotions, easy avoidance of people and the hint of immortality are tempting. However, the movement away from an embodied, empathic, creative and authentic self seems like a horrible existence. The collective momentum towards integration between humans and machines poses some important questions and choices to be made. Yet before moving too far ahead we must become intimate with ourselves and question the life we want to live before we enter into a serious human-machine relationship.