I share your facination with empathy failures, when worked through, I think these ultimately provide the richest learning experiences that psychotherapy can offer. When not worked through, it can be quite hurtful to patients and can leave therapists in a demoralized state.
I graduated with my doctorate four years ago. My internship was at a college counseling center and after graduation I stayed on part-time as a therapist. During my internship year I worked with a student who was bright and artistic and had an unusual ability to uncover all of my insecurities as a novice therapist. My superviser was extraordinarily helpful and my client made tremendous developmental gains over the course of the year. When the school year concluded, it was a final termination, as I had no plans to return to the counseling center the following year.
Approximately half way through the second year, my client, now a junior, dropped by my office. On the spot, it was difficult to know how to react. Was he stopping by to say hi or did he want to return for therapy? In addition, I had another client scheduled in 15 minutes and didn't have enough time to talk to him. I said I would be happy to schedule him in and gave him the next available time. He later left a message cancelling the appointment and didn't return for the rest of the year.
In my last year of part-time work at the counseling center he made an appointment. He was now a senior. We worked together for the academic year. Time was spent analyzing what had transpired the year before. He said he had felt disappointed in my reaction when he returned. He said it was like having great memories of a summer at camp, then returning the following year to find it was not at all like you remembered. To oversimplify greatly, in navigating the continuum of optimal distance I had been too distant. Undoubtedly, shame about my own positive feelings for my client contributed to this disconnection and may well have triggered shame in him about his (seemingly) unreciprocated positive feelings.
Ultimately, I have found that the relational model developed at the Stone Center to be the most useful way of clarifying empathic failures. In particular I have liked Judith Jordon's chapter called "Female Therapists and the Search for a New Paradigm" published in Michael Sussman's 1995 book called A Perilous Calling: The Hazard's of Psychotherapy Practice. I also found a chapter by Sue Elkind called The Impact of Negative Experiences as a Patient on My Work as a Therapist in Barbara Gerson's 1996 book called The Therapist as a Person: Life Crises, Life Choices, Life Experiences and Their Effects on Treatment to be a very interesting account. The author recounts some powerful negative experiences as a client and describes how this led her to become a therapist who also functions as a consultant for therapist-client impasses.
Working through empathic failures can be a healing process, and from a relational perspective, this can lead to a transformation of relational patterns both in and out of therapy. I heard a great presentation by Lorna Smith Benjamin a few months ago who remarked that "Your children can heal you, if you let them". Similarly I believe our clients can teach us, if we let them.