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The present work seeks to explore the potential of the dialogue as a pedagogical instrument. While the dialogue as a form of theory transmission underpins the Western philosophical canon, too few attempts have been made to transpose this model to psychoanalysis. Through the intersubjective exchange of perspectives within a fictitious scenario, the dialogue allows one to explicate, challenge, and compare theoretical positions without necessarily having to ultimately privilege or defer to any one idea or thinker. Therefore, it is potentially well-suited to psychoanalysis which, as a field, is continually searching for ways to accommodate a plurality of perspectives to counteract a tendency towards sectarianism. In this present experiment, a broadly Freudo-Lacanian theory of signification is put into conversation with a late Wittgensteinian-Rortian one via a discussion between a man and a woman who run up against the limits of language as they try to speak of death, love, and truth. The thought of Alain Badiou, Donald Davidson, Slavoj Žižek, and Martin Buber also figures alongside these two central currents.