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Today’s easy online access to personal information has redefined the concepts of privacy, disclosure, and boundaries in all forms of relating. The impacts of this on the therapy relationship have also been examined, but almost exclusively in the context of patients pursuing online information about their therapists. In line with the contemporary relational view of therapy as a two-person model, this article aims to address and explore the reverse; in other words, therapists pursuing the readily available online information about their patients. While it is considered clinically inadvisable for the therapist to seek out more information than what the patient chooses to provide, therapists sometimes privately act on their desire to know more about their patients through checking social media accounts or Googling them. Like many other “secret delinquencies” of therapists, it seems that this behavior is kept in the closet; it is not talked about, thus depriving us of the opportunity to examine it and learn from it. This article first explores how and why it clashes with the analytic contract in an effort to bring a more exploratory rather than critical approach to what otherwise might simply be considered wrong. Then, it aims to examine the complex relational dynamics surrounding this behavior and candidly address some of the deeper questions it raises. Case examples as well as a qualitative review of therapists’ personal accounts are used in an effort to situate this particular type of delinquency in a theoretical and clinical context.