Hilario, federal inmate 05994-070, says that an 18-year-old Swift emailed him in January 2008 to request a Skype meeting because "she was lonely and sad and that she needed someone to chat with." That initial email apparently blossomed into a months-long friendship by Hilario's estimation. For non-fans, that would be about the time Fearless came out, Swift's second release. Her first album, 2006's Taylor Swift, has sold 5.5 million copies since its release and debuted at number 19 on the Billboard 200 chart.