My recognition of Paul Ornstein’s outstanding contributions to psychoanalytic theory and practice cannot be overstated. But there’s a special place in my heart for his work on Dostoevsky. For decades Paul has immersed himself in Dostoevsky, reading all of his novels and writing several articles. I wanted to pay tribute to this work but in the available time (or in any amount of time) I knew I wouldn’t write an article that could stand next to Paul’s profound and scholarly articles on Dostoevsky (Ornstein, 1993, 2012). In this necessarily smaller project I am, therefore, responding to Paul’s work on The Brothers Karamazov by exploring Chekhov’s Three Sisters, undertaken in a tragicomic spirit that (I hope) will honor both Paul Ornstein and Anton Chekhov. I shall look at the characters in Three Sisters, especially their feelings of loss and longing—the sources, modes of expression, or ways of warding off such feelings.