A revealing documentary suggests Prince Andrew and Ghislaine Maxwell may have dated. A timeline of their friendship shows they often traveled and partied together.

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Prince Andrew Ghislaine Maxwell
Prince Andrew and Ghislaine Maxwell are seen attending Royal Ascot in 2000.Tim Graham Photo Library via Getty Images
  • A documentary suggests that Prince Andrew and Ghislaine Maxwell may have dated.

  • The Duke of York previously said Maxwell had introduced him to disgraced financier Jeffrey Epstein.

  • A timeline of their friendship shows Prince Andrew and Maxwell were frequently spotted together in the late '90s and early aughts.

A revealing documentary has shed light on Prince Andrew's relationship to Ghislaine Maxwell, the British socialite who was sentenced to 20-years in prison for sex-trafficking underage girls for disgraced financier Jeffrey Epstein.

Two sources who were interviewed for the ITV documentary "Ghislaine, Prince Andrew and the Paedophile" said that Andrew and Maxwell were so close that Buckingham Palace staff believed they dated at one point in the early aughts.

It was also in the early 2000s that Epstein victim Virginia Giuffre alleges Epstein and Maxwell made her sleep with Prince Andrew on multiple occasions when she was 17. Giuffre is currently suing Prince Andrew over allegations that he sexually assaulted her at Maxwell's London home, at Epstein's New York home, and on Epstein's private island.

Prince Andrew has denied the allegations, and says he doesn't recall ever meeting Giuffre. One day after losing a bid to get Giuffre's case dismissed last week, the Duke of York was stripped of his royal patronages and military titles, and informed he would have to defend himself in the lawsuit as a private citizen.

Prince Andrew has long been tied to Epstein through his friendship with Maxwell, but there's still a lot we don't know about his association with the convicted sex trafficker. Here's a timeline of their friendship as documented in news reports and interviews over the years.

Prince Andrew met Maxwell when she was at university

Prince Andrew said in his infamous November 2019 interview with BBC Newsnight that he'd known Maxwell since her university days.

Maxwell attended Oxford, graduating in 1985, a time period during which the Duke of York was serving in the Royal Navy.

Maxwell also came from a well-connected family. Her father, Robert Maxwell, was the owner of the Daily Mirror newspaper and a one-time member of Parliament before his death in 1991.

The pair were often spotted together in the late 90's and early aughts

Maxwell and Andrew seemed especially close in the late 1990s and early 2000s, when their outings on the New York and London social scene were widely covered in the press and the friends were often pictured together.

  • February 1999: Flight logs obtained by the Daily Mirror show Andrew flew with Maxwell aboard Epstein's private jet to the financier's private Caribbean island, Little St. James.

  • Late summer/early autumn 1999: Prince Andrew hosts Maxwell and Epstein at Balmoral, according to a model who attended the getaway and later spoke to the Daily Mail.

Jeffrey Epstein Ghislaine Maxwell
A cache of images introduced at Ghislaine Maxwell's trial includes a photograph of her and Jeffrey Epstein relaxing at what appears to be Balmoral, Queen Elizabeth's royal residence in the Scottish highlands.US Attorney's Office for the Southern District of New York
  • February 2000: Andrew vacations at Mar-a-Lago with Maxwell before attending a fashion show in New York, according to a 2001 article in The Evening Standard.

  • April 2000: Andrew makes another trip to New York where he "socialized with Ghislaine," according to The Evening Standard.

  • May 12, 2000: Flight logs again show Andrew flying aboard Epstein's private jet from New Jersey to Palm Beach, Florida, with Maxwell also on board.

  • June 21, 2000: Epstein and Maxwell attend a party at Windsor Castle, partially in honor of the prince's 40th birthday, according to the BBC.

  • June 22, 2000: Andrew and Maxwell are pictured attending the Royal Ascot.

  • September 2000: Andrew and Maxwell are pictured together at the Wiltshire wedding of the prince's former girlfriend, Aurelia Cecil. Pictures show the two arriving at the wedding in the same car, according to the BBC.

  • October 31, 2000: Andrew and Maxwell were pictured together at Heidi Klum's Halloween party in Manhattan.

  • December 2000: Andrew hosted Maxwell and Epstein at Sandringham for a "straightforward shooting weekend," according to his 2019 BBC Newsnight interview.

  • January 2001: Andrew takes a trip to Thailand with Maxwell, according to The Evening Standard.

Maxwell and Epstein were believed to be dating at some point during this era. At Maxwell's child-sex-trafficking trial last month, Cimberly Espinosa testified that she worked at Epstein's company from 1996 to 2002, largely as Maxwell's executive assistant. Espinosa said that when she first started at the company, she believed Epstein and Maxwell were dating, but she got the impression they broke up sometime in the last two years of her employment at J. Epstein and Co.

A former Buckingham Palace royal protection officer says Maxwell visited so often that he suspected she and Prince Andrew were dating

Prince Andrew and Maxwell may have started dating around 2001, according to Paul Page, a former royal protection officer who spoke for the ITV documentary.

Page said he first met Maxwell in 2001, and that Buckingham Palace staff suspected Andrew and Maxwell had an "intimate relationship" by the frequency of her visits.

"From the way she was allowed to enter and exit the palace, at will, we realized … suspected, that she may have had an intimate relationship with Prince Andrew," Page said. "A colleague of mine remembered her coming in four times in one day from the morning till the evening — she kept coming in and out, in and out."

Another source who spoke on the program was Euan Rellie, a banker who said he also became friendly with Maxwell during university.

"I got the sense that Prince Andrew and Ghislaine had probably been girlfriend and boyfriend in the past," Rellie said in the documentary, according to the Telegraph. "They had an easy warmth around each other."

Prince Andrew's press office did not respond to Insider's request for comment on the claims in the ITV documentary.

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