Reasoning by default is a relevant aspect of everyday life that has traditionally attracted the attention of many fields of research, from psychology to the philosophy of logic, from economics to artificial intelligence. Also in the field of law, default reasoning is widely used by lawyers, judges and other legal decision-makers. In this paper, a philosopher of language (Carlo Penco) and a philosopher of law (Damiano Canale) attempt to explore some uses of default reasoning that are scarcely considered by legal theory. In particular, the dialogue dwells on the notion of literal meaning, witness testimony, and the problem of disagreement among experts in legal proceedings. The paper is intended as a sort of brain storming useful to identify new lines of research straddling philosophy of law, cognitive psychology and philosophy of language.