It has been acknowledged that education includes ‘a love of what one teaches and a love of those whom one teaches’ (Hogan 2010: 81), but two traditions of writing in philosophy of education—concerning love for student and love for subject—have rarely been brought together. This paper considers the extent to which the ‘triangular’ relationship of teacher, student and subject matter runs the risk of the rivalry, jealousy and strife that are characteristic of ‘tragic’ love triangles, or entails undesirable consequences such as transference from one intended object of love to another. It argues that this faultline in the literature of educational love corresponds to education's ‘divided heart’. The implication of this exploration of education's triangular relationship is that we cannot ignore the ‘dark of love’, nor can we address it simply by asserting that educational love must be of a more honourable sort than romantic love. These tensions can be reconciled through the loving recourse of ‘ceasing to strive’ and the possibility of sublimating the two originary loves into a higher ‘love of truth’.