This paper asserts the current age as perverse, a social paradigm facilitated by explosive technological progression that is rapidly altering the erotic and social dimensions of human relationship. The author employs psychoanalytic and evolutionary theories to explain the ease with which we humanize machines and dehumanize people. The quest and need for love, which combines both discovery and invention, is framed within Winnicott’s concept of the transitional object. A detailed case is presented of a man who lived with a high-end love doll. The case illustrates his simultaneous need to dehumanize women and humanize the doll, as well as his use of the analyst to help him transition from being with a doll to being with a human partner. Questions regarding technology’s growing impact on the future of relationships are surfaced.