Two of the most influential thinkers of the last century, Marcel Proust (1871-1922) and James Joyce (1882-1941), met in 1922 but had little to say to each other. Had circumstances been different, what might they have said? They had much in common, including an interest in doctors and diseases, but from different perspectives. Although the meeting was a lost opportunity to explore the insights of two great analysts of the human condition, their lives and works provide a record rich in detail and timeless in relevance. From this, we construct what might have been overheard during a conversation between Marcel Proyce and James Joust almost a century ago.