In this study I suggest ways of thinking through issues of intimacy that have emerged in the late twentieth and early twenty-first centuries in the USA. I propose a state of intimaphobia in education. However, I move beyond exposing this state of intimaphobia to offer particular readings of two philosophers of intimacy: Michel Foucault and the Marquis de Sade. I argue that these two philosophers provide alternative models of thinking through the problems and potentials of and for intimacy. While Foucault has been taken up within education in any number of ways, his concept of the "homosexual" is utilized to offer insights into intimacy. Sade, while the stranger philosopher to engage, offers challenges to contemporary educational practices through the lessons of the libertine. Foucault and Sade offer, to put it simply, promises for pedagogical pleasures that challenge the current fears around intimacy in education.