Inside Prince Andrew’s tawdry love life

Before his fall from grace, the Duke of York managed to get involved with a very unlikely slew of women.

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Late last month, we hit a historic royal milestone and the world didn’t notice. January 28 marked the 475th anniversary of the death of King Henry VIII, a monarch who is more famous for his disastrous personal life, in which I’m including cleaving England away from the Catholic Church in the name of lust-slash-love, than anything else.

(It’s hard for any union to work when one half of a relationship is all too willing to have the other’s head lopped off when the going gets tough.)

If ever there was a member of the reigning house for whom their personal life has, similar to Henry, landed them in infamously hot water it is Prince Andrew, former Falklands War hero, former grasping British trade ambassador and current all-round pariah.

Sarah Ferguson, Duchess of York and Prince Andrew, Duke of York on June 21, 2019 in Ascot, England. Picture: Max Mumby/Indigo/Getty Images

These days the only time Andrew is seen in public it is when he is beetling up and down the roads which connect his home in Windsor Great Park, Royal Lodge, with his Mummy’s big house nearby (AKA Windsor Castle), often with his ex-wife Sarah, Ferguson, the Duchess of York by his side.

However, despite her steadfast support, a fact which might lie more in base necessity than anything else, Andrew is a man with a very chequered dating history which has seen him pick up during taxpayer funded official trips and for a former Sports Illustrated model to have to deny he was the father of her child.

Let’s take a tawdry trip down memory lane, shall we?

The ‘understudy’

It will be 40 years exactly this month since Andrew began the most serious relationship in his life, aside from his marriage. It was February 1981, and American actress Koo Stark (who later claimed she had been up for the role of Princess Leia in Star Wars) was in London where she was an understudy at a National Theatre production of Who’s Afraid Of Virginia Woolf?

As Stark later wrote of the origin of their romance: “Friends, including the landlady of my basement flat in Chester Square, Belgravia, were taking Prince Andrew for a meal but the ‘spare girl’ had gone missing. It turned out I was her understudy too.”

When they arrived at the restaurant, “we crashed into each other before both swiftly stepping back. The same thing happened a second later. ‘I am a Prince, I go first,’ he said,” she recounted.

“Being American, I retorted: ‘I am the Prince’s date, I go first,’ but he got his foot into the door just ahead of me, chuckling. We immediately had an easy familiarity.”

(He sounds like such a charmer, no?)

Prince Andrew with his then girlfriend, Koo Stark.

Later, he “secreted a note which I found the next morning on my rustic Biedermeier dresser. ‘Come to BP tomorrow for lunch,’” Stark recounted.

“Initially I wondered why he was taking me to a petrol station – it took me a moment to realise he meant Buckingham Palace. I went.

“We had lunch on trays in the nursery which was the suite of rooms where he and Prince Edward had grown up, but was by then his flat in the Palace.”

Andrew and Stark’s romance blossomed and for months they managed to keep their relationship a secret, even when she started bringing her pet parrot Candy with her to visit him at his ‘BP’ apartments.

In 1982, when Andrew returned the conquering hero after having flown helicopters during the Falklands War, she travelled to Scotland to stay at the Queen’s private estate Balmoral and then the couple flew to Mustique where they stayed at Princess Margaret’s island home.

Actor and photographer Koo Stark in 1989. Picture: Alpha Agency

By now, the news that the Queen’s second son was dating the glamorous American had broken.

“We used to be able to walk around London without much attention. Andrew’s private detective looking furtive in his dark suit drew more sideways glances than we did.

“We were watched 24 hours a day, chased, harassed, libelled, lampooned and tormented.”

In the Caribbean, “the paparazzi were flying over low in light aircraft or swimming up to the beach in scuba gear,” Stark has said.

Then, 18-months after they had started dating, news broke that Stark had previously starred in the films The Awakening of Emily and Cruel Passion, based on the Marquis de Sade’s novel Justine, which included some racier scenes and which were incorrectly labelled ‘sort porn’ by some at the time.

(In 2019, Stark successfully sued MTV’s parent company after their website referred to her as a “porn star”.)

Their relationship did not survive the ensuing scandal and Buckingham Palace put out a statement at the time that said: “We do not know if the Queen was aware of the girl’s acting career before she was invited to Balmoral.”

Despite all of this, the pair has stayed close with Andrew taking on godfather duties for Stark’s daughter Tatianna.

The convicted sex trafficker

While Ghislaine Maxwell’s name has now become inextricably linked to that of Andrew’s, it has always been in the context of them as friends. However earlier this year, former royal protection officer Paul Page alleged that the duo enjoyed a far intimate bond.

Prince Andrew, Virginia Giuffre, and Ghislaine Maxwell posing for a photo. Picture: US District Court – Southern District of New York (SDNY)/AFP

“From the way she was allowed to enter and exit the palace at will, we realised – suspected – that she may have had an intimate relationship with Prince Andrew,” Page told the documentary Ghislaine, Prince Andrew and the Paedophile.

“A colleague of mine remembered her coming in four times in one day. She kept coming in and out, in and out.”

The PR supremo

British PR Aurelia Cecil, who sold her company for millions in the late ’90s, occupies something of a bit part in the Andrew dating annals. Little is known about their time together, which happened in the years after Andrew’s divorce, but it’s worth noting that the most frequently used photo of Andrew with Maxwell was taken at Cecil’s 2000 wedding at which they were both guests.

The reality TV star

Caroline Stanbury in 2005. Picture: Jo Hale/Getty Images

Caroline Stanbury might be better known these days as a star of the short-lived reality series Ladies of London but at the turn of the millennium it was her ties to Andrew which saw her make news.

In 2000 the pair reportedly dated, including him taking her to a soiree on Martha’s Vineyard with then President Bill Clinton and First Lady Hillary Clinton. According to The Sun, the media’s interest in the pair ultimately led to their split.

The one-time Playboy model

Turns out 2000 was a busy year on the romantic front for Andrew with him later meeting Denise Martell, a former Playboy model and actress the same year during a taxpayer funded trade trip to Los Angeles.

Denise Martell, Mail on Sunday front page from 2001. Picture: Mail on Sunday

She later revealed to The Mail on Sunday that they had spent two nights together, saying: “The nights I was alone with him in his room he never had any security with him.

“I had only just met him. But I walked straight to his room. I knocked on the door and he opened it.

“He’d given me his room number, his code name, his private mobile phone number, everything.

“He gave the mobile number to me on the first night after I’d only known him a few hours. There was never any security there. I was very surprised. I was shocked. The President would never have been left alone like that. I was worried for him.”

Here comes quite the weird bit: According to the Mail, Martell also revealed that at one point he “stripped down to his boxer shorts and allowed Denise to tuck him into bed.”

Riiiight…..

(His very curious bedroom moves also includes “modelling girlfriends’ underwear by way of a joke,” The Independent reported in 2006.)

The businesswoman he wanted to marry

Now we get to Amanda Staveley, a highly successful businesswoman about whom the Duke of York was so serious he is reported to have popped the question.

Andrew met Staveley in 2001 during a meet-and-greet that included the then King of Jordan. Immediately smitten with the blonde, reportedly, he asked for her number and the pair dated for the next two years with things getting so serious she spent time at Buckingham Palace and Sandringham.

Stavely even got the royal seal of approval.

“Prince Philip adored her company and let it be known in the family that he considered her to be ‘an ideal choice’ as the next Duchess of York,” the Daily Mail has reported.

Prince Andrew reportedly proposed to Amanda Staveley.

She is also said to have met his daughters Princess Beatrice and Eugenie who liked the glamorous Yorkshire-born then 30-year-old.

However, things fell apart when Andrew reportedly decided he wanted to take things to the next level and he proposed. Staveley, understanding the sacrifices that her new life and title would demand, turned him down.

“Andrew’s a lovely man and I still care for him a great deal,” she told the Daily Mail in 2008. “But if I’d married him, my independence would have disappeared.”

The Sports Illustrated model

Angie Everhart and Andrew are reported to have met sometime around 2003 after meeting in, again, LA.

Everhart told the Daily Mail in 2009 that she met the Prince through her former father-in-law George Hamilton, who in turn had met the royal at a party.

“George and I had remained on good terms after my divorce from Ashley and when George called to ask if I’d like to go for dinner with a Prince, of course I said yes.

“George told me, ‘He likes redheads and he has a wish list of girls he’d like to meet while he’s in town – and you’re on it.’”

Clearly a man who is happy to move fast, the following day the statuesque model and the HRH had their first date. “We started talking and we got along and he was lovely. He’s so charming and probably the most innocent and naive person I know,” she has said.

Angie Everhart dated Prince Andrew around 2003.

The unlikely pair was last photographed together in 2008, seen zipping around in his Aston Martin.

One of the most fascinating things that Everhart revealed in that Mail interview is the role that Fergie played in her former husband’s love life, saying that anyone he might date needs to get the Duchess’ “stamp of approval.”

“Andrew tells you right at the beginning that Sarah and the girls are the most important women in his life and they need to like anyone he dates,’ she recounted.

“It was important to him that they approved of me. I went to England and stayed at Royal Lodge.’ I count Sarah as a friend. You can’t be friends with one without the other. It’s impossible. They are like two peas in a pod.

“I’ve met Sarah several times and she’s just charming. Totally friendly.”

In 2009, when Everhart welcomed her son Kayden, she clarified during a UK interview that ‘Kayden’s daddy is someone who is not in the public eye,” and that “he lives in Manhattan Beach, not in a palace in London.”

1000 women

File this one under a “Gross” with a capital ‘G’. In 2019, a longtime friend of Andrew’s told The Sun that the former naval officer had slept with “way over a thousand” women.

“He doesn’t drink, he doesn’t smoke and he doesn’t take drugs and never has, but sex is his big thing in life,” the friend said.

“He was known as Randy Andy for a reason when he was younger and it’s never really stopped.

“Travelling all over the world as the UK trade ambassador and for other royal duties has given him access to some beautiful women and he’s taken full advantage.

“He is a red-blooded male and, if you like, he is like a sailor with a girl in every port.”

As I said, gross.

Maybe desperate, definitely dateless

Two years after Everhart’s interview about Kayden, the now infamous photo of Andrew with his arm around then 17-year-old Ms Giuffre emerged along with the similarly notorious shot of the royal with by then convicted sex offender Jeffrey Epstein.

In the decade since then, Andrew’s years of being linked to such a colourful slew of women has come to a pretty abrupt stop and the only woman he is now regularly seen with is his ex-wife.

Given he is facing a civil trial in New York later this year over claims that he raped Ms Giuffre on three occasions, an allegation he has strenuously denied, it’s hard to imagine there are many women queuing up to date the now toxic “private citizen”.

Daniela Elser is a royal expert and a writer with more than 15 years experience working with a number of Australia’s leading media titles.