Representational views of language and communication view ambiguity as a problem to be solved. An alternative approach treats ambiguity as an opportunity to challenge, skirt, and reinvent received knowledge and identity. In so doing, this approach makes a connection between epistemology and ontology, linguistic and existential meaning. This article describes this perspective on language and communication and offers three practical examples of how resources of ambiguity can be used to flirt with new, different notions of self and the world.