With recent leaps in large language model technology, conversational AI offer increasingly sophisticated interactions. But is it fair to say that they can offer authentic relationships, perhaps even assuage the loneliness epidemic? In answering this question, this essay traces the history of AI authenticity, historically shaped by cultural imaginations of intelligent machines and human communication. The illusion of human-like interaction with AI has existed since at least the 1960s, when the term “Eliza effect’ was named after the first chatbot Eliza. Termed a “crisis of authenticity” by sociologist Sherry Turkle, the Eliza effect has stood for fears that AI interactions can undermine real human connections and leave users vulnerable to manipulation. More recently, however, researchers have begun investigating less anthropomorphic definitions of authenticity. The expectation - and perhaps fantasy - of authenticity stems, in turn, from a much longer history of technologically mediated communications, dating back to the invention of the telegraph in the nineteenth century. Read through this history, the essay concludes that AI relationships might not mimic human interactions but must instead acknowledge the artifice of AI, offering a new form of companionship in our mediated, often lonely, times.