The meaning of “taboo” has changed. In today's media landscape, race, politics, nudity and sex work are discussed more openly than ever before. At the same time, platforms and publishers have to cover these issues in a thoughtful, non-triggering way—all while navigating comment moderation. With massive adoption of Snapchat and Facebook Live giving individuals and brands power to broadcast widely and instantly, audiences are exposed to images and headlines in real time, leaving publishers and platforms in a position of deciding where to draw the line. How do we define the new taboo? Who wins the #freethenipple battle? And as a business, can we talk taboo without scaring off brand partners?