Caroline Stanbury once dated Prince Andrew, a.k.a. "Randy Andy." After his divorce from Sarah Ferguson in 2000, Stanbury and Andrew were in a relationship, despite their age difference. According to Metro, the 40-year-old British prince took twenty-something Stanbury to a gala in Martha's Vineyard hosted by Bill and Hillary Clinton. The outlet reports the royal relationship didn't last because of the pressure of the media spotlight.
Stanbury's parents are old friends of the Duchess of York's father Major Ron Ferguson's ex-wife, and Fergie reportedly had strong feelings about her ex dating young Stanbury. An inside source told The Daily Mail that the press attention might not have been the reason for the split. A friend of the prince told the Mail, "It was either the publicity or Fergie putting her foot down."
It was probably just as well that things didn't work out with Andrew, who settled a sexual abuse lawsuit against him in February. In her book, "The Palace Papers: Inside the House of Windsor — the Truth and the Turmoil," royal expert Tina Brown called the prince "a coroneted sleaze machine." Brown told Time, "He's clearly a dim bulb, there's very little going on upstairs, and he's something of an oaf ... Unfortunately, being intellectually dim and surrounded by sycophancy is a very bad combination."