The author explores some ways that we help patients to hold paradoxical realities intrinsic to transference and play in analytic work. He suggests that Winnicott’s guardianship of the setting for the emergence of playing raises questions about the role of neutrality in an ontological analysis. The author tries to demonstrate some ways that the work of helping patients to hold paradox in play overlaps with a concept that he has earlier referred to as an activity of neutrality. He explores how in the analytic process, understanding and being are two dimensions of the analytic process that work in concert with each other. Often the analyst works quietly in spaces between epistemological and ontological approaches in the holding of paradox.