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The purpose of this work is to share my thoughts as an English teacher, using John Dewey’s works on education, art, and democracy to examine the topic of artificial intelligence (AI). I used a diffractive reading technique to read Dewey on art and education through the words of Marc Andreessen on the same topics. In diffractively reading, I was attuned to “which differences matter” and where those differences pointed (Barad, 2007, p. 378). The diffractive reading revealed the isolating and anti-democratic nature in the discourse around AI, especially as it applies to use in schools and on children, suggesting a need in education for critical application of theory and a slowing of technological implementation in classrooms and curriculums.