Introduction: Recently Baggs and Chemero (2018. "Radical Embodiment in Two Directions." "Synthese," 1-16. doi:10.1007/s11229-018-02020-9) advocated for the possible 'productive synthesis' between the enactive and the ecological approaches in order to understand and to explain how an agent behaves and interacts with the environment. This paper argues that data production methods from 'enactive anthropology' and 'ecological dynamics' show complementarities and differences that can inform research and pedagogical applications. Purpose: From the analysis of two studies of pedagogical interventions, we explore the potential of intertwining enactive anthropology and ecological dynamics approaches in Physical Education. Methods: We summarise two previously published studies, which address skill learning through the intertwining of phenomenological and behavioural outcomes. The first investigates the interactions between students engaged in orienteering during PE lessons, the second focuses on learning climbing skills during an individual lesson. We utilise the data to highlight the advantages and limitations of intertwining enactive anthropology and ecological dynamics approaches. Findings: We suggest caution in using principles of both approaches together, due to key epistemological and ontological differences, which may impact data outcomes and preferred methodologies. The approaches differ in conceptualising the nature of individual-environment coupling but may be complementary in investigating the complexity of this coupling. Conclusion: We assert the scientific potential of intertwining enactive anthropology and the ecological dynamics approaches and the need to consider this productive synthesis to propose practical implications for PE teachers. The outlines of a pedagogy 3E (exploration, experiential and empathetic) from intertwining these two approaches are traced.