Psychoanalytic theory and practice have moved toward privileging relational and attachment dynamics as both cause and cure of many of the issues that bring individuals into psychoanalysis and psychotherapy, highlighting the significance of each therapeutic relationship as a key part of the work. But, what is that relationship? We are not parent/child, nor are we friends, but a deep, mutual bond often develops and enhances the process. Fantasies of being friends, emanating from either and/or both participants, can represent important, often unformulated, aspects of this relationship. Psychoanalytic theory has not fully explored meanings of this wish to be friends, but it is my experience that finding ways to reflect on a wish or fantasy to be friends can lead to deeper and more complex understanding of adult attachment. In this article, theory and clinical examples will be utilized to examine resistances as well as contradictions, conflicts, and hopes and fears that come into play when thoughts, fantasies, and wishes to be friends to enter the therapeutic space.