Drawing on social systems theory, we aim to advance traditional views on dialogue by introducing a paradoxical perspective. The paradox of dialogue is the possibility and im-possibility of understanding. Using different approaches to unfold the paradox, we propose matrix of conversational dynamics that include the classical view on dialogue and extends it by introducing a third element. We illustrate two different third elements - an alternative per-spective and the immersion in a different site – and show how these can promote the emergence and acceptance of new distinctions that help to unfold the paradox of dialogue.