Empathy was introduced to philosophy as a solution to the problem of other minds skepticism, the doubt whether other minds exist at all, which arises from the Cartesian dualist picture of the mind as metaphysically hidden (Lipps 1907). Already in Lipps’s work, and from then on into contemporary philosophical discussion, empathy in its various forms is commonly seen as our way to know what specific minds believe and feel and desire in specific scenarios. In this paper, I focus on affective empathy, usually seen as the success of a simulation effort, where one tries to adopt the perspective of another and imagine oneself in the other’s situation (e.g. Coplan 2011). I shall argue that this attempt is resting on a misguided notion of similarity between two people, and that the epistemic stance simulation involves is objectifying and obliterating of the other’s individuality. Relying on the work of the psychoanalyst Neville Symington (2018), I propose a new associative-imaginative account of affective empathy, which involves the surrender of the epistemic position and a genuine moment of a communion in feeling.