This article studies two charities. Their volunteers shared a feeling of compassion for the homeless and an egalitarian spirit, but compassion is a two-sided phenomenon with respect to equality: it can either underline the common humanity of the benefactor–unfortunate dyad or breed feelings of condescension and shame. Moreover, if and when volunteers successfully accomplish their good intentions, the fact that their gift expects no return could reinstate inequality – hence, the ‘charity paradox’. I show that one organization resolved the paradox by promoting situational equality in the volunteers’ conversations with the poor, while the other reduced interactions to a server–served relationship.