This article examines the thematic and stylistic similarities between the poetry of Rosario Castellanos and the paintings of Frida Kahlo. In their poems and seíf-portraits, these two Mexican artists used root imagery to represent union and separation. They also shared a fascination with medical discourse and the representation of broken bodies. Through an interdisciplinary analysis of these themes and images, we discover a constant pairing of incompatible opposites and the emergence of two similar theories of how to live with pain.