This paper sheds light on an issue we all face, how to work with differences encountered in our everyday interactions with each other when the outcome of the exchange is not simply up to us. Our contribution lies in proposing the notion of anticipational fluidity, of finding ways of relating and responding to others as we orient ourselves to each other and to what might happen next within the moment of conversation. Situated in a hermeneutic lens that highlights the interplay of interpretations in unfolding responsive moments, we integrate the work of Shotter and Ricoeur with our interpretation of empirical texts generated from an ethnographic inquiry of academic/practitioner collaboration. We suggest that anticipational fluidity encompasses open work, difference-making and tentative intentionality, and elaborate these sensitizing resources by putting readers within unfolding moments of a meeting where differences are addressed.