This paper characterizes the self-disclosure behavior of Reddit users across 11 different types of self-disclosure. We find that at least half of the users share some type of disclosure in at least 10% of their posts, with half of these posts having more than one type of disclosure. We show that different types of self-disclosure are likely to receive varying levels of engagement. For instance, a Sexual Orientation disclosure garners more comments than other self-disclosures. We also explore confounding factors that affect future self-disclosure. We show that users who receive interactions from (self-disclosure) specific subreddit members are more likely to disclose in the future. We also show that privacy risks, due to self-disclosure, extend beyond Reddit users themselves to include their close contacts, such as family and friends, as their information is also revealed. We develop a browser plugin for end-users to flag self-disclosure in their content.