The social entrepreneurship (SE) discourse habitually casts social entrepreneurs as heroic, creating economic and social value, whereas those whom they strive to assist are portrayed as disadvantaged and in need of interventions. This implies an implicit differentiation between knowing, agentic entrepreneurs and less-knowing, more passive beneficiaries. In this article, we seek to unfold the subtle ordering of relations in SE and problematize power-related aspects and ideological influences that potentially overshadow dimensions of mutuality and relationality inherent to SE. From an examination of two cases, we hypothesize that differentiations between knowing selves and learning others tend to disintegrate when entrepreneurs and beneficiaries enter into closer interaction. Adopting a postcolonial framework, we identify three forms of relations in SE: transactional, ambiguous/interactional and transcending.