This paper explores relations between human conundrums and psychoanalytic technique and theory through the relationship between Freud and Ferenczi. Rather than vilify (or lionize) either figure, the paper seeks to see into their struggles and conflicts, and to draw from correspondence and writings a portrait of a relationship. The paper describes not two dusty figures drawn from the closet of history but rather two live, flawed, and struggling human beings whose rational ideas about what they were doing could never keep step with their emotions. There is therefore much to be learned from their relationship: about transference and countertransference, about boundaries and friendship, about rivalry and despair, and about shame.