Caterpillar, a new podcast hosted by author Chris Stedman, tells the story of Alex, a man who died by suicide at 31 years old. When he died, he scheduled personalized emails to go out to a group of family members and friends. At the end of one of these emails, the one sent to the host of this show, was a link to a private SoundCloud page with audio files of him talking to a mysterious woman he met on a Britney Spears fan forum named Alice. A woman whose voice sounds exactly like Spears herself. Who was this person? What was she getting out of talking to Alex, and what did he get out of talking to her? In the wake of Alex’s death, Stedman tries to understand who this person was, Spears's significance to Alex more broadly, and how at one point this mysterious online stranger might have helped Alex feel understood and connected—as well as how Alex did the same for him and others.