Different representational systems permit differing degrees and forms of ambiguity and underspecification in the content they represent. Independently of this observation, a notable feature of natural language as a representational system is that it allows the same content to be expressed in different ways. In this paper, we examine the interaction of these two observations; in particular, we explore a number of linguistic forms involving underspecified content, and look at how subjects express the content of these linguistic forms both in logic and in diagrams. Our analysis demonstrates that variations in syntactic realization of the same semantic content lead to different interpretations of that content.