There have been many debates about psychoanalytic and Jungian views of homosexuality. As part of these it has often been recognized that analysts have appeared reluctant to comment on their own countertransference responses to gay patients. Yet these responses must inevitably have a significant bearing on the way the work is conceptualized and undertaken. This paper highlights ways in which homophobia and related countertransference difficulties influenced the author's ability to engage with one male patient. It traces the process by which the analyst became aware of his own discomfort and the nature of his struggle to find a more helpful and reflective position in the analytic work. The process was prompted by a dream which depicted some of the difficulties the analytic pair was experiencing and by a heightened scrutiny of the countertransference. The progress of the work is marked by three further dreams which trace the development of the analytic relationship.