While in eighth grade, Debbie fell in love with and started dating Dudley Scott. They continued dating through high school.
In 2012, after the Van Ness House was added to an Internet list of Most Haunted Places in America, Debbie and Dudley decided to spend a romantic night in the house. As they made out, they heard Annie Hawkins' car approach and hid, fearing that she was the police. While they were hiding, the two teenagers were approached by the ghost of Dexter O'Connell who attempted to scare them into leaving. Dexter failed and Debbie and Dudley were murdered by the ghost of Whitman Van Ness who crushed their hearts. Their bodies were found by Annie moments before she suffered the same fate.
Following their deaths, Debbie and Dudley were left trapped as ghosts stuck in the Van Ness House. While Annie's ghost conversed with the ghost of Bobby Singer, Debbie and Dudley walked past the two together. Annie called out to them, but the couple ignored Annie and continued on their way. Shortly afterwards, two of their friends entered the house to film a memorial to their love story only to be killed themselves.
Debbie and Dudley's bodies were eventually found by Annie and Bobby. After the Winchesters dispatched Van Ness, Bobby led them to the corpses of Van Ness' victims and the Winchesters salted and burned them, putting the ghosts of all of Van Ness' victims to rest.