Abstract: Internet users notoriously take an assumed identity or masquerade assomeone else, for reasons such as financial profit or social benefit. Butoften the converse is also observed, where people choose to reveal truefeatures of their identity, including deeply intimate details. This workattempts to explore several of the conditions that allow this to happen byanalyzing the content generated by these users. We examine multiple socialmedia on the Web, specifically focusing on Yahoo Answers, encompassingmore than a billion answers posted since 2006. Our analysis coversdiscussions of personal topics such as body measurements and income, and ofsocially sensitive subjects such as sexual behaviors. We offer quantitativeproof that people are aware of the fact that they are posting sensitiveinformation, and yet provide accurate information to fulfill specificinformation needs. Our analysis further reveals that on community questionanswering sites, when users are truthful, their expectation of an accurateanswer is met.