We will briefly describe a unique case of Mr. L who saw five therapists with whom he has attended eight psychological treatments altogether. A series of in-depth interviews were conducted to explore his copious negative experiences and complaints. The data were analyzed using Interpretative Phenomenological Analysis. The results offer an insight into how these negative effects echo the patient’s basic issues that brought him to psychotherapy, resonating with Arkowitz and Lilienfeld’s thought that “people who seek psychotherapy for conditions that cause them serious distress often thwart the very help they seek.” However, we strived to carefully analyze how both the patient and his therapists could have contributed to the development of these negative experiences and ponder some implications for the therapeutic practice.