There is a phrase that social pedagogues employ time and again to characterise contextual thinking in everyday practice: ‘it depends … ’. This is often used when seeking answers akin to a formula that can be applied across situations; but can leave the listener with the thought that socio-pedagogical explanations are woolly or even incoherent. Yet when aware of context, pedagogues are clear about specific actions they take and can articulate the reasons behind such actions. What are the underlying principles, assumptions about the nature of reality, of humanity and of relationships that shape such an attitude? Dialectical epistemology and ontology assume that reality is in constant motion, that contradictions are the driver of that process of change. Further, understanding comes from highlighting relationships between different entities rather than separating them from their context. In this article, I use concepts taken from activity theory – a Marxist theory of learning using dialectical thinking – to articulate the relationship between particulars of everyday situations that are the bread and butter of socio-pedagogical practice. By showing that both activity theory and Freire’s Pedagogy of the Oppressed have the same philosophical basis, I argue that these commonalities have explanatory potential for social pedagogues when ‘it depends … ’. I hope that this will encourage practitioners interested in social pedagogy to expand their understanding of the importance of the philosophical assumptions behind their work, and join the work needed to further explore the development of social pedagogy within an activity theoretical framework.