Why do our digital systems break people? Conversational AI tools like Grok or ChatGPT are promoted as a means to democratize knowledge and expand access to information. In practice, however, they have also made sexual harassment easier, reproduced harmful stereotypes, and, in some cases, encouraged people to self-harm rather than helping them. These outcomes are not rare glitches. They reveal how conversational AI and social media platforms are built, governed, and deployed at scale.