Dating AI is "a meditation on how to prepare for the unknown," a thought experiment designed to stimulate new ideas about issues that are important now as well as in the future. Fictional descriptions of human-android romances are interspersed with commentary about the varying differences between people and AI (Artificial Intelligence), and methods for breaching the chasm between machine and human experience. Chapters tie speculation into contemporary life, drawing parallels between current human interactions with machines. Section 1, "Are you ready to fall in love with a machine?" explains what you'll need to know to engage romantically with AI (including similarities and differences). Section 2, "You are ready, now what?" helps interested humans prepare to date AI. Section 3, "Establishing a relationship" covers the complicated mix of human and AI needs in a relationship, including power dynamics and acceptable behavior. Section 4, "Getting over a breakup (or merger)" explains some of the legal and economic fallout that could result from the demise of an human-AI breakup. Dating AI is an entertaining, humorous (even slightly satirical) exploration: not only of a possible future, but also of our rapidly changing present relationships with other people and technology. Discerning readers will be compelled to utilize their imaginations, again and again, in an attempt to depict the Psychology of the Future, which looks to be significantly different from anything Freud might have considered. To quote the visionary writer J.G. Ballard, "Sex times technology equals the future." Just as almost nobody predicted the Internet until it suddenly seemed to have ensnared all within its grasp, so the technology of AI may, sooner than we think, come to be as natural as breathing, and inevitably, perhaps deeply, ensconced in our unconscious -- to be revealed in our dream life as we fall asleep at night. Dreams reveal truths far beyond what the rational mind might consider "tolerable." It is only at the borders of acceptability where our future freedoms reveal themselves, adumbrating and perhaps incubating a society of the future, where science and art seamlessly integrate themselves, and where poetry and technology are no longer alien domains but a vast cultural continuum where play and discovery create new language and, ahem, acceptable behaviors! We shall see...