The Unauthorized Biography Finding Freedom: Harry and Meghan and the Formation of a Modern Royal Family delves into a rift between Prince Harry and one of his close friends, Tom Inskip. Harry met Inskip or “Skippy” (pictured) while attending Eton College, and the two were Daily mail. According to the outlet, Skippy was even dating Harry during the Las Vegas incident in 2012 when Harry was “caught playing nude pool with showgirls in a hotel suite.” Needless to say, the two men go back a long way.
When Harry started dating Meghan Markle in earnest, Skippy apparently had his reservations and, according to the biography (about the Daily mail). While Skippy’s comments “came from a good place,” the king “didn’t quite see it.” A source told the book’s authors (via The Telegraph): “It really hurt him that someone he was so close to wouldn’t trust his judgment.”
According to the biography, Harry eventually barred Skippy from a very important event at his wedding reception.