After being invited by the editors Stefanie Schneider and Hubertus Kohle (LMU Munich) to contribute a chapter to their book, Similarity: Concepts of the Digital, Jon Emmony and I conceived the idea of a conversation between ourselves and Chat GPT (as a collaborator) based on our project Infinite Loop (2022). The book, Similarity: Concepts of the Digital, centres on the idea of Similarity as an elementary phenomenon that manifests itself as the correspondence of objects on the basis of shared characteristics, and Due to its complexity, the conceptual system of similarity is embedded in a dynamic interplay of culturally shaped and individual perceptions that must continually be recontextualized. This volume brings together perspectives from the natural sciences, the humanities, and the arts, and shows how similarity is operationalized algorithmically and how similarity-generating patterns become productive within the digital image. This project is overseen by the DFG ( Deutsche Forschungsgemeinschaft (DFG), the German Research Foundation) and is part of a priority programme “The Digital Image” which examines, from a multi-perspective standpoint, the central role attributed to the image within the complex process of the digitization of knowledge. It is located within a nationwide research network across Germany, the aim is to develop a new theory and practice of computer-based image worlds.