Results of the Boston University Mellon Sawyer seminar 20162-019 (www.mellophilemerge.com) reveal that social and philosophical drives are increasingly central to our uses of technology, including AI. This raises critical challenges for democracy, especially in a hyper-connected world where social media shapes human conduct in ways we are only beginning to appreciate. A history of the mutual impact of Turing and Wittgenstein on one another points to the contemporary foundational significance of our artful capacity to embed everyday words in forms of life. Wittgenstein's mature focus on forms of life, interlocutory drift, and rule-following, with its play between the 'I' and the 'we', was an informed critical response to Turing's idea of a 'Turing machine', his analysis of the very idea of taking a 'step' in a formal system. Wittgenstein's characterisations of our drive to evade a responsibility in speech, especially by appealing to 'machines' or 'algorithms' as pure mathematical objects, are invaluable warnings for us. The enduring importance of mutually-attuned 'phraseology' to education may be formulated as a humanistic challenge to the very ideas of 'computational foundations' and 'Big Data' in our hyper-connected world.