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Internet users notoriously take an assumed identity or masquerade as someone else, for reasons such as financial profit or social benefit. But often the converse is also observed, where people choose to reveal true features of their identity, including deeply intimate details. This work attempts to explore several of the conditions that allow this to happen by analyzing the content generated by these users. We examine multiple social media on the Web, specifically focusing on Yahoo! Answers, encompassing more than a billion answers posted since 2006. Our analysis covers discussions of personal topics such as body measurements and income, and of socially sensitive subjects such as sexual behaviors. We offer quantitative proof that people are aware of the fact that they are posting sensitive information, and yet provide accurate information to fulfill specific information needs. Our analysis further reveals that on community question answering sites, when users are truthful, their expectation of an accurate answer is met.