Anonymity forms an integral and important part of our digital life. It enables us to express our true selves without the fear of judgment. In this paper, we investigate the different aspects of anonymity in the social Q&A site Quora. The choice of Quora is motivated by the fact that this is one of the rare social Q&A sites that allow users to explicitly post anonymous questions and such activity in this forum has become normative rather than a taboo. Through an analysis of 5.1 million questions, we observe that at a global scale almost no difference manifests between the linguistic structure of the anonymous and the non-anonymous questions. We find that topical mixing at the global scale to be the primary reason for the absence. However, the differences start to feature once we "deep dive" and (topically) cluster the questions and compare the clusters that have high volumes of anonymous questions with those that have low volumes of anonymous questions. In particular, we observe that the choice to post the question as anonymous is dependent on the user's perception of anonymity and they often choose to speak about depression, anxiety, social ties and personal issues under the guise of anonymity. We further perform personality trait analysis and observe that the anonymous group of users has positive correlation with extraversion, agreeableness, and negative correlation with openness. Subsequently, to gain further insights, we build an anonymity grid to identify the differences in the perception on anonymity of the user posting the question and the community of users answering it. We also look into the first response time of the questions and observe that it is lowest for topics which talk about personal and sensitive issues, which hints toward a higher degree of community support and user engagement.