The authors reflect on their ongoing dialogue about connections between drawing in the practice of art and in the practice of mathematics. They show how visualizing relational connections in mathematical diagrams can be used to contextualize aspects of Heath’s drawings. The account provides a sequence of loops, reflecting on drawings where relational marks coexist with those in which they do not. Diagrams are the vehicle for this dialogue across the disciplines of art and science, acting as boundary objects supported by a common visual vocabulary of loops, connections, change over time, negative space, and a shared interest in exploring ideas through the physicality of practice.