“I am willing to talk to you,” Marla responds to Monte upon his request for supervision. The arrogance overwhelms Monte. The words reverberate in his head. Monte, disturbed by this interaction seeks help from me in psychotherapy. “Yep, it sounds like arrogance,” I affirm. “Why does the grandiosity bother you so much?” I ask Monte. “We are colleagues. I am asking for help, but she treats me like she is doing me a favor.” Monte says with internal turmoil which appears to exceed the current interchange. “You are so disappointed with Marla, over and over again. Why do you keep going back for more disappointment?” I ask, thinking that Monte might be replaying an experience in his life where he gets his hopes up, only to be met by crashing devastation. “I really don’t know,” Monte says, almost pleading with himself to come up with an answer. “Maybe you feel you deserve to be disappointed.” I say, trying to gently suggest that he set himself up for this by calling her up. “Maybe,” Monte tentatively says, with a sense of personal disgust in his voice. “I am willing to talk to you too,” I say, trying to make light of this situation as the time comes to an end. We laugh, but we know the pain is still there.