This paper compares the careers of the writer Samuel Beckett and the psychoanalyst, Wilfred Bion. Their lives crossed during the years 1934–35, when Beckett was in treatment with Bion. I argue that there is a common set of concerns that shapes the writings of these two men as well as similarities in form and content. I suggest that a certain modern paradigm underlies the work of the two thinkers: the breakdown of attempts to maintain connexions, whether interpersonal connexions or logical connexions. Both Beckett and Bion struggle with how to connect in the face of this catastrophic breakdown in meaningful connexion. I hypothesize that a certain kind of 'imaginary' twinning relationship developed between the two, and that each used the brief actual contact with the other to help sustain the effort at exploring the pain of non-meaning and non-connecting.