In this paper, we explore the paradox of trust and vulnerability in human-machine interactions, inspired by Alexander Reben's BlabDroid project (2012–2018). Under this project, small, unassuming robots successfully elicited personal secrets from individuals, often more effectively than human counterparts. This phenomenon raises intriguing questions about how trust and self-disclosure operate in interactions with machines, even in their simplest forms. We study the change of trust in technology through analyzing the psychological processes behind such encounters. The analysis applies theories such as Social Penetration Theory and Communication Privacy Management Theory to understand the balance between perceived safety and the risk of exposure when secrets are shared with AI. Additionally, philosophical perspectives such as posthumanism or phenomenology serve as a means for engaging with these broader questions concerning privacy, trust, and what it means to be human in the digital age. Rapid incorporation of AI into our most private areas challenges us to rethink and redefine our ethical responsibilities.