The morning after Prince Andrew’s disastrous BBC interview, he achieved the nearly impossible: steering the national conversation away from Brexit after three interminable years. But serious questions remained. Had the eighth in line to the throne just lied through his teeth, or was he guilty of spectacularly bad judgment?

I have met Andrew several times over the years, and his reputation as a blundering and arrogant buffoon is not without foundation. One of my friends described him as a man with “all the airs and graces of royalty, but none of their superiority—he lacks Eton charm.” I witnessed this boorishness firsthand at a lunch I attended in his honor in the mid-aughts in Condé Nast U.K.’s Vogue House boardroom, hosted by the division’s then head, Nicholas Coleridge. Andrew was awkward and uneasy in a group conversation, but that didn’t stop him from giving an unsolicited 30-minute monologue to the eight editors present on the difficulties of reversing a tanker into port. He was so clearly used to being heard that he never learned to listen or to read the room.

“Andy, Darling!”

But Andrew’s sexual appetite—or, more precisely, his desire to be wanted—was always his most troubling blind spot. It was on full display at a dinner party I attended alongside him in London in the late 90s. Our hosts were a British art dealer and his exotic foreign wife, who was reputed to have once been a madam in New York. Respecting protocol, my fellow guests and I bowed and curtsied to the duke when he arrived. But then something odd happened. Sexy young women, introduced to us as models, joined the crowd. Instead of formally greeting the prince, they flung their arms around him, crying, “Andy, darling!” They clearly knew him well. As soon as one left his lap, another would take her place. Like a pasha, he sat back and let them come to him. The rest of us, with our conservative airs and old-world propriety, felt foolish. But what I remember above all about this most unusual experience was the look on his face. It wasn’t that of a creepy, sex-obsessed man—he looked more like a dumbfounded adolescent.

As soon as one left his lap, another would take her place.

In a way, Andrew is not dissimilar to many well-born British men. Shipped away to boarding schools at an early age, they are fenced off from both their families and members of the opposite sex, which can impact their emotional development. Andrew’s lifelong incarceration within the rigidly observed confines of the royal family, coupled with a lack of self-awareness, a constant entourage of fawning yes-men, not to mention a reduced position as second son, meant he was disadvantaged from the start. He is a man without a point, and I suspect no one feels that quite as keenly as he does.

Eyes wide shut, mouth wide open: left, Prince Andrew at a party thrown by Hong Kong financier Andy Wong in 2002; right, at a British Olympic Association dinner in Beverly Hills in 1984 with, from left, Dudley Moore, Julie Andrews, and Tom Jones.

In the course of writing this article, I spoke to several of his friends, both male and female—some of 30 years standing and some with whom he has been intimate. All requested anonymity. Overall, two unanimous and firmly held opinions immediately emerged. The first, that Andrew would have had no idea that the girls he met through Epstein were being trafficked and ordered to sleep with him; the second, that Andrew almost certainly did sleep with Virginia Roberts (an allegation he has strenuously denied). “Of course he did” was everyone’s immediate answer. “He has always chased a shag,” said one, who should know, because she once shagged him herself.

In his 20s, Andrew spent 18 months dating the actress and photographer Koo Stark, but his 1986 marriage to Sarah Ferguson brought a brief period of stability and two adored daughters, Beatrice, 31, and Eugenie, 29, both popular members of the royal family. But when Ferguson embarked on an alleged affair and they eventually divorced, in 1996, Andrew was once again at sea, without a solid or consistent group of friends to steer him. He fell in with a fast, glamorous crowd, and that’s when the trouble started.

“[Royals] actively seek out the rich,” said a member of his social circle at the time. “Every penny they spend has to be accounted for, so they can’t afford private planes or yachts, and that’s why you always see them on other people’s planes and yachts. They love free holidays. I’m not surprised Andrew was so easily seduced by [Jeffrey] Epstein, with his vast array of influential friends. The girls around him were not the main point, but they were definitely his Achilles’ heel.”

He is a man without a point, and I suspect that no one feels that quite as keenly as he does.

A former stylist he dated—let’s call her “Lucy”—observed his attraction to women who were far outside of his royal circle. He was once associated with a native Californian who worked as a lingerie model before transitioning into acting and producing. (She was named Maxim’s International Woman of the Year for three consecutive years, and she produced and starred in Debbie Does Dallas: The Musical.) “Andrew was told, ‘You can’t hang out with people like her,’ and he replied, ‘Why not?’ He has a total lack of emotional intelligence,” said Lucy. She recalled with annoyance his tendency to introduce himself to her friends as “the Duke of York,” “even when we were dancing on tables at two in the morning at Momo [a popular Moroccan restaurant in London with a basement club]. It struck me how impressed he was with who he is, or how impressed he wanted others to be. Every joke always ended with ‘ … because I’m the Duke of York!’ He tells the most pathetic jokes. He finds poo cushions funny.”

Left, a 25-year-old Prince Andrew in 1985 with 39-year-old Vicki Hodge, who had appeared in the film Confessions of a Sex Maniac. Right, with Koo Stark in 1998. The two dated in the early 80s.

In terms of his behavior as a boyfriend, Lucy says, “He was respectful. Sexually, a little keen, but perfectly straightforward. There was a bit of chasing around the sofa, but not in an aggressive way. I remember, one day, looking out of his Buckingham Palace bedroom window and thinking, ‘What a sad life.’ People were standing outside the gates 24/7.” The highlights of their short-lived relationship were movie nights at home on her sofa. According to Lucy, Andrew would eat popcorn, although he did not consume alcohol or, curiously, garlic. (Fun fact: his e-mail address at the time was [email protected]—.com.) One of the duke’s other favorite pastimes? Hitting the massage table. “[Andrew] said he was particularly fond of four-handed [massages], where two women work on you at the same time,” said Lucy. “When mention of a foot massage came up in the [BBC] interview, I immediately thought, Yes, that’s him.”

His e-mail address at the time was [email protected]—.com.

Despite all this, Lucy still describes him as “always gentlemanly” and that there was “nothing awful or sneaky about him,” except when it came to paying the bill, which he and his entourage conspicuously avoided. “I suggested one evening that we go to the cinema. He said, ‘Great, how many tickets have you bought?’ I was slightly taken aback, so I said I would buy two, but he said we would need seven in total to include his security.”

Lonely, but Not Alone

When Lucy eventually ended the relationship, she says, the duke was exceptionally gracious about the whole thing—“to the point where I wondered what else was going on,” said Lucy. “I think he’s still a little in love with Fergie. She has some kind of hold over him. He always told me he would never get married again. He’s basically a loner, with no real friends, and it was obvious that he’s not close to his siblings.” Revealingly, Lucy says, “He once told me, ‘I just got off the phone with the future King of England.’ He was talking about William. It was almost like he was impressed.”

But then again, it didn’t take much to dazzle the Duke of York. He was frequently befriended by enablers, one of whom once invited him, along with a group that included models, on a trip where massages were plentiful. Another man who was present on the excursion recalls an uncomfortable situation. “It was just me, Andrew, and two women in a spa room,” he says. As the man retreated from what he believed to be a developing threesome, one detail couldn’t help but catch his attention. “I thought to myself, Well, at least he has a big cock.”

Vassi Chamberlain is an Editor at Large for Air Mail based in London