Privacy issues on social media are becoming an increasing area of concern. Paradoxically, some netizens are actively divulging their privacy online. Noticeably, some information is specifically guilt-related, though confession online is considered irrational. This preliminary study strives to understand this guilty information disclosure behavior through a mixed-approach. Analyzing posts and comments in a confession forum on Reddit, we find that sex-related and recreation-related topics prevail. Our qualitative investigation produces a thematic model with 71 codes, 17 concepts, 4 frames, 3 categories, and 9 relationships, capturing the intents, content, influencers of this behavior, and the interactions among users. Our contribution relies on the investigation of this peculiar behavior to better understand people’s privacy behavior. Also, we render a sophisticated framework around guilt-inducing behaviors useful for future work. We also suggest it as a mixture of conformity and counter-conformity, a modern “technology of self” and a variant of Adaptive Cognitive Theory.