It will probably surprise no one that many of the theorists writing on the role of love in education today locate the power of love in its “transgressive” or “disruptive” character — that is, in the negative role it may play against or within the bureaucratic, inhuman structures of schools. The rhetorical force generated by arguments based in the negative character of love in education may be related to our inability to positively define what the personal relationships between teachers and students ought to be or to allow, but it would be a mistake to think that theorists of love in education are limited to this sense of indefiniteness. As this essay seeks to set out, love in education is mostly theorized under two categories of negativity that provide a normative conclusion against the limits placed upon both teachers’ and students’ humanity by current policies and practices. In the following pages, I examine these categories, which I refer to as “absence” and “transgressivity,” by focusing on how negativity plays a role in each through their opposition to current norms in schools. Using this analysis as a starting point, I explore the idea that “love in education” might be understood as more than a tool with which we might condemn or attack schools from without. Instead, I question whether the lack or emptiness that theorists find when they look for love in education might be a different sort of negative altogether, namely, the original lack that marks human desire. This constitutive negativity, I argue, stands as distinct from theories based in love’s capacity to transgress or disrupt educational norms, because it serves as the very foundation of educational relationships. By applying Jacques Lacan’s construction of desire, as a slippage between the subject’s primal needs and ability to express them in language, to Jane Roland Martin’s concept of the “love gap in education,” I hope to show that the gap she recognizes as an absence of love in educational practices and theories is one that provides the basis for any educational relationship, and one that may provide us with an explanation of other theorists’ concentration on negativity in speaking of love in education.