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This article investigates new relations with things that are expansive and inclusive of the pluralities and differences within our entanglements with technologies. We do this by extending our commitments to the methodological approaches of material speculation and co-speculation that led us to engage in multi-year conversations between ourselves as design researchers, philosophers, and a counterfactual artifact we designed, known as a Tilting Bowl. The philosophers lived with the Tilting Bowl during this period. We call these conversations, polylogues, of which the aim is to co-speculate on a range of new possible relations by which to consider living with technological things. The contributions of our article are two-fold. Firstly, through our polylogues, we offer descriptions of three relations with things. These include 1) non-anthropocentric care: care that is non-anthropocentric and existential; 2) non-presumptive relations: not-knowing in relating to and engaging with things; and 3) ideologized relations: ideologies that frame relations with technologies. Secondly, the article elaborates and critically reflects on co-speculation as a method for relational and situated knowing that can be of benefit to HCI researchers.