With so many figurative references to the heart, the heart has become an overextended metaphor and threatens to become less meaningful. Widely circulated books on Critical Pedagogies and Contemplative Pedagogies refer to the heart. Though they may share a sense of learning as transformation, each has a very different method, which I identify as dialectical or dialogical.  And, each one defines its liberatory transformation in a very different way, one with “third space” and the other in relational and holistic space, which is considered transcendent. This essay describes two forms of heartfelt awareness, first-order heart-based knowledge and the heart’s second-order regulatory function. Then, through the lens of the heart’s regulatory function, it examines the differences between Critical and Contemplative Pedagogies. I do so in order to articulate, through the form and function of the actual heart, a model for how to measure the way contemplative and conventional philosophies of education might come together for transformative education.