This chapter looks at what made craigslist personals distinctive from other online dating platforms, focusing on shifting norms around anonymity and a persistent social stigma. More than any other section, the personals demonstrate a Web 1.0 vision of social connection, where experimentation and risk were valued over trust infrastructure. Craigslist's politics of openness and inclusion were contested most fiercely when it came to sex and dating, demonstrated by legislation like Fight Online Sex Trafficking Act (FOSTA) as well as the tendency to stigmatize craigslist personals and the people who use them. Like newspaper classified ads of the past, craigslist personals were often viewed suspiciously by the general public, sensationally by the media, and as a gateway to the margins by academics. By being so open and accessible, craigslist invited spectators and voyeurs, as well as critics. Stigma here emerges as a response to the gap between social expectations of sex and dating and the messy, shady, serendipitous reality of the web.