In this article, I consider how the psychoanalytic situation functions to facilitate, but also to inhibit, the intimate, loving connection that develops between analyst and patient. The article is a meditation on the intricate interplay of possibility and limitation in psychoanalysis. My thesis is that the very factors that make therapy safe enough, and rich with possibility for the deepest interconnectedness, can also exert a constraining influence on our work. The clinical approach I am most interested in exploring involves an engagement of certain loving capacities, including those of discernment, critical thought, committed challenge, generosity of spirit, and acceptance.