Zeugma (“The storm sank my boat and my dreams”) is a well-recognized figure of speech whose mechanism of operation is less well understood. We suggest treating zeugma as a breach of syntactic iconicity: the syntactic form of the coordinative construction statement implies an equivalence or semantic proximity between the two objects of the verb (boat and dreams), while the objects supplied are semantically very distant. Unlike nominal metaphors and similes, in zeugmas two metaphorically-related, nonsymmetrical objects are put in syntactically symmetrical positions. This feature, the breach of iconicity, registers as a surprise, an effect wholly different from that of metaphors and similes. Seeing zeugma in these terms makes it possible not just to explain its functioning beyond broad pronouncements about yoking together different items, but to tease apart syntactic and semantic factors that contribute to the level of the breach of iconicity and subsequently to the zeugma’s strength. Moreover, understanding zeugmas as a surprising breach of iconicity leads to the question of how this breach may be accommodated or made sense of. In the second part of the essay, we introduce three types of accommodation strategies, each with a distinct focus: the language, the objects, and the speaker.