This dialogue addressed the “Not Interesting” and the “Boring” in contemporary architecture through the lens of two books, one by Andrew Atwood and the other by Paul Preissner. It moved between the specific ideas put forward by Atwood and Preissner and a broader conversation about the nature of our attentional economy and media conditions, including exhaustion with spectacle, novelty, and the constant demand to create distinctive and spectacular forms. The dialogue also attempted to wrestle with the irony, or contradiction, of a sophisticated “high” avant-garde discourse about “low,” banal, and dumb things.