Twentieth-century philosophy has often been pictured as divided into two camps, analytic and continental. This study challenges this depiction by examining encounters between some of the leading representatives of either side. Starting with Husserl and Frege's fin-de-siècle turn against psychologism, it turns to Carnap's 1931 attack on Heidegger's metaphysics (together with its background in the Cassirer-Heidegger dispute of 1929), moving on to Ayer's 1951 meeting with Bataille and Merleau-Ponty at a Parisian bar, followed by the 'dialogue of the deaf' between Oxford linguistic philosophers and phenomenologists at the 1951 Royaumont colloquium, leading up to the Derrida-Searle controversy. Careful study shows that it is implausible to assume the existence of a century-old 'gulf' between two sides of philosophy. Vrahimis argues that miscommunication and ignorance over the exact content of the above encounters must to a large extent be held accountable for any perceived gap.