Prince Harry's former girlfriend reportedly made a bold prediction about him. According to evidence given byjournalist Barbara Jones in the Duke of Sussex's privacy trial against the British press, Chelsy Davy - who dated Harry on-and-off from 2004 until 2011 - thought he could turn out like Andrew Mountbatten-Windsor. The writer allegedly recruited a man named Joe Osman, who claimed to be friendly with Davy's brother because he sold him cannabis. Chelsy Davy and Prince Harry dated on and off for a few years.