“To consent to love or be loved,” said Merleau-Ponty, “is to consent also to influence someone else, to decide to a certain extent on behalf of the other.” This essay explicates that idea through a meditation on intimacy. I propose, first, that, on Merleau-Ponty’s account, we are always transgressing into each other’s experience, whether we are strangers or familiars; I call this “ontological intimacy.” Concrete experiences of intimacy are based upon this ontological intimacy, and can take place at two levels: (1) at-this-moment (such that we can experience intimacy even with strangers, by sharing a momentary but extra-ordinary mutual recognition) and (2) in shared interpersonal institutions, or habitual, enduring, and co-enacted visions of who we are, how to live, and what matters. Through particular examples of dynamics within these layers of intimacy (drawing upon work by Berne and by Russon), I claim that we are always, inevitably, imposing an “unfreedom” upon our intimate others. Freedom, then, can only develop from within and by virtue of this “unfreedom.” Thus, what distinguishes empowering or emancipating relationships from oppressive ones is not the removal of transgressive normative social forces; it is rather the particular character of those transgressive forces. Some transgressions upon others’ experience—some forms of “unfreedom”—will tend to promote freedom; others will tend to hinder it. This amounts to a call for promoting agency and freedom not only through critical analysis of public institutions, practices and discourses, but also through critical insight into and transformation of our most private and intimate relationships.