In this paper, through a Gadamerian hermeneutical analysis of Sartre’s and de Beauvoir’s letters while Sartre was away at war, as a written example of their amorous philosophical dialogue, and their later works as products of this dialogue, I show how they failed to achieve “authenticity” in their own relationship as they themselves defined it. Specifically, I address this failure precisely with regard to both the complete synthetic unity of consciousness and as absolute individual freedom, especially within their relationship of love. This failure of Sartrean existentialism to handle intimacy causes the entire system, supposedly formed from experience, to crumble.