In All’s Well That Ends Well, Shakespeare imagines a common enough situation—someone you love, if ambivalently, will never love you—and in doing so suggests how unrequited love might become an art, a practice of sustaining relationship with those who prefer no relationship whatsoever and who might not merit our investment to begin with. How, Shakespeare asks, can you have a relationship with someone whose heart is corrupt and who, anyway, would prefer to flee? Shakespeare’s answer: by making scenes, and, it turns out, by being a masochist. Helena’s art, I argue, indeed looks forward to the art of masochism as outlined by Gilles Deleuze. For Deleuze, the works of Sacher-Masoch outline an art defined not in the familiar Freudian sense, by finding pleasure in pain, but by a masochistic constellation manifested in scenes of disavowal, suspense, and waiting.