This report offers an interpretation of recent scholarship that articulates pasts and futures of geographical thought and praxis. By focussing on growing concerns about speculative, abyssal, and analytical styles of thinking in Geography, I argue that a more cogent philosophical take on geographic theory-making is needed. Drawing upon ongoing discussions on the role of geographic theory, I use the occasion of the various history and philosophy of geography-related anniversaries to reflect on why we are where we are today. I therefore claim that practitioners of history and philosophy of geography need to address some structural difficulties to navigate tensions between recurring calls for endogenous forms of geographic theory and relentless deconstruction of epistemic and ontological arrays as a way forward for Geography to merge with critical thinking.