The author offers an intensive clinical study, in which the paradox of termination is illuminated. For this patient, termination repeats the schizoid problem for which he arrived in treatment. The fear of closeness is confirmed by the knowledge that closeness will inevitably lead to loneliness and loss. This treatment dilemma opens up an inquiry into the original formulation of the analytic situation. The author proposes that the structure of psychoanalysis—intimacy entwined with the severing of intimacy—may conceal a need-fear dilemma which lies at the heart of our practice. I propose that this dilemma has always been gendered. Resistance to termination has been “feminized,” and a willingness to terminate has been “masculinized.”