Sharing sensitive information online, such as one's sexual identity or medical information, can be a complex decision. Many people do not share sensitive information out of fear of being stigmatized, yet sharing can be beneficial for a variety of reasons. This study examines two instances of sensitive disclosure within the SAA (same-sex attracted adolescents) community: people revealing their LGBTQ+ status on social media and revealing the use of an anti-HIV medication, pre-exposure prophylaxis (PrEP), on both social media and dating platforms. By examining these two disclosure decisions, we can better understand how designers can support sensitive disclosure. Ultimately, results suggest that designing for disclosure doesn't mean designing to get people to explicitly disclose, but rather enabling users to subtly communicate sensitive information. Moreover, rationales for disclosing sensitive information play out differently between social media and dating platforms.