Sarah Ferguson's Secret Nicknames for Her Crushes Revealed — What Did She Have in Common With John F. Kennedy Jr.?

In the 1990s, two kinds of royalty orbited the same spotlight. Sarah Ferguson, newly separated and under scrutiny, and John F. Kennedy Jr., America’s political prince. According to a new biography, when their paths almost crossed, the duchess had already given him a private codename.

A fresh burst of claims about the Duchess of York’s post-royal years, drawn from Andrew Lownie’s biography “Entitled: The Rise and Fall of the House of York” and echoed in a wider serialised account of her spending and hustles, has unearthed a detail so brazen it feels ripped straight from a 1990s rom-com.

When Ferguson set her sights on John F. Kennedy Jr., she did not just flirt with the fantasy. She filed him.

In her rarefied world, lovers and near lovers were not merely remembered. They were catalogued, coded, and quietly ranked.

The codename, Lownie writes, was “Number Nine", Kennedy’s “place in the order of her lovers”. A footnote in the book lays out the roll call around him, with Prince Andrew listed as “Two”, John Bryan as “Three”, followed by a string of names and numbers that reads like a diary scribbled in tantalising shorthand.

It is a startling image: a British duchess treating romance like a private scoreboard.

And yet, in a strange twist of fate, it was also something she had in common with the man she so avidly pursued.

He was American political royalty, widely hailed as the era’s most eligible bachelor. She was royal by marriage, newly separated, attempting to survive on the fading glow of a title that still opened doors, even as debts mounted and headlines snapped at her heels.

A Crush With a Code Name

According to Lownie, Ferguson’s fascination with Kennedy flared during a trip to New York.

She asked staff to find out if he was in town and, once they discovered his whereabouts, she invited him for drinks or dinner at her hotel, The Carlyle. He accepted.

Then came the complication and the almost breathtaking confidence.

When Ferguson was told Kennedy had a girlfriend, actress Daryl Hannah, she replied, “That’s not going to bother me!” Lownie says it did bother Hannah, and Kennedy cancelled, citing a prior engagement.

Undeterred, Ferguson allegedly ordered staff to watch his apartment through the night to see if he was telling the truth.

One close confidante, quoted in reporting around Lownie’s book, insisted the fixation was anything but casual:

“It’s incredibly real to her, like a schoolgirl crush. She spends hours talking about him. The fact that she’s never even met him doesn’t seem to matter at all.”

That portrait of a woman breathlessly infatuated sits alongside the far less flattering sketch painted elsewhere in Lownie’s broader work on the House of York.

In the Daily Mail serialisation of his Prince Andrew biography, Ferguson is described as ambitious and financially reckless, living lavishly while creditors circled, and leaning heavily on her royal connection to keep business, charity, and celebrity ventures afloat.

The Kennedy obsession was not an isolated anecdote. It slotted neatly into a wider pattern: a woman performing constantly, craving reassurance, and believing that a big enough name might rewrite her narrative.

At that moment in the 1990s, Kennedy was exactly that sort of name.

Why Kennedy, Why Then

The decade cast Kennedy as an American prince, the famous grin, the famous surname, editing George magazine while basking in Camelot’s glossy afterlife.

For Ferguson, newly separated in 1992 and repeatedly criticised for her money-making ventures, he symbolised something intoxicating, an escape hatch.

Lownie alleges she spent "hours scouring magazines for articles about" Kennedy, "cutting out pictures of him in his swimming trunks," and asking friends whether he would approve of different facets of her personality. One confidante recalled her suddenly asking,

“Do you think Ken will mind that I don’t like such and such a thing?”

To those around her, it was utterly real.

Kennedy carried his own burden of projection. Even as a working editor, his image did half the work. The son of an assassinated president, he existed inside a national memory whether he wished to or not.

In that paradox, Ferguson and Kennedy mirrored one another. Their lives were endlessly narrated by others, yet both depended on attention, glamour, and curiosity to keep their worlds spinning.

The Diana Factor

The drama sharpened when Princess Diana entered the picture.

Lownie says Ferguson was “not to be discouraged”, particularly after learning Diana had met Kennedy for 30 minutes at Christmas 1995 in a New York hotel. Ferguson was furious, snapping:

“He’s mine! Why can’t she just leave him alone?”

A separate account in “JFK JR: An Intimate Oral Biography” adds another layer. Kennedy’s former executive assistant RoseMarie Terenzio and People editor at large Liz McNeil quote Patrick Jephson, Diana’s private secretary and equerry, explaining why the meeting was kept quiet:

“It was never made public, so that made it quite fun, actually. Diana wanted it to be discreet because it had all the makings of a great gossip story, didn’t it?"

At the time, he was widely regarded as the world’s most eligible bachelor, and she had just separated, or was in the process of separating. It was the sort of pairing that would have fuelled endless speculation.

She did not want that narrative to take hold, though she was curious to meet him. And, in part, Jephson suggested, there may have been a competitive edge, as Sarah Ferguson was known to have a crush on him and Diana may have been keen to outmanoeuvre her.

A Pattern of Public Crushes

Kennedy was not alone in Ferguson’s reported orbit of longing.

Lownie details other “amorous obsessions”, including actor Kevin Costner, golfer Tiger Woods, and George Clooney. Yet the Kennedy episode stands apart for its system, the codename, the ranking, the sense of a private cabinet of fantasies.

He was not merely a movie star. He was, like Sarah Ferguson, shaped by family legacy as much as personal accomplishment.

By then, she was living with the uneasy aftermath of a royal marriage, a title that still dazzled, and a reputation that critics claimed had curdled into scandal, spending, and relentless deal-making.

In its harshest telling, she leveraged “HRH The Duchess of York” branding while pleading poverty, blurred charity and commerce, and pursued an expensive lifestyle even when the money was not there.

In that context, the Kennedy fixation reads less like a joke and more like a pattern.

He was powerful, glamorous, and globally admired. Aligning herself with that image, even in fantasy, offered distance from the criticism closing in around her.