Ideas of relationality have come to influence a wide range of theoretical fields. In this article, we develop an understanding of relationality as not necessarily something continuous and uninterrupted (as is often the case), but rather as something fundamentally shaped through breaks and interruptions. We work through notions of relational brokenness by "thinking with" the telephone as an intriguing relational technology, a material metaphor, and a discursive device. The argument moves between Derrida's telephone fascination; the metaphorical black telephone in Sylvia Plath's poem "Daddy"; Proust's narrator waiting for a call from his grandmother in "The Guermantes Way"; and the communication breakdown in Lady Gaga's "Telephone." What the telephone allows for in this discussion is a way of thinking of not only technology as inherently fractured, but also our very ways of relating, connecting, and being in the world.