This article was first presented as a plenary paper at the Annual Meeting of the International Association of Psychoanalytic Self Psychology in October 2013. In keeping with the theme of the conference, “forms and transformations of connectedness,” the article summarizes my nine-year analysis with “Linda,” a patient who was intensely conflicted about allowing the kind of deep connection I believed was necessary for her to make the kinds of changes she ostensibly was in therapy to achieve. The clinical narrative focuses on our dialogue and struggles around this issue as it evolved through different phases and relational configurations.