Back in 1974, at a fancy dinner party in Manhattan, two very different worlds collided.
Barry Diller, the ambitious movie executive, met Diane von Furstenberg, the Belgian fashion icon known for her iconic 1970s wrap dress.
But their first encounter was far from romantic.
Diane, who was already married to German playboy Prince Egon von Furstenberg, barely gave Barry the time of day — and her husband even mocked Barry’s short trousers.
Yet, just months later, the story flipped completely.
When Barry and Diane met again, the spark was undeniable.
What started as a chance meeting soon blossomed into a passionate affair, marking the beginning of one of America’s most powerful and unusual couples.
A Love Fueled by Passion and Complexity
Barry Diller, then a 32-year-old head of Paramount Pictures, recalls that second meeting as a whirlwind.
“There was a glow around us that was setting off sparks,” he wrote in his new memoir, admitting that his attraction to Diane was almost primal.
Their chemistry was electric — so much so that within a day, they were inseparable, making out on Diane’s lavish Manhattan sofa.
Despite their deep connection, their relationship wasn’t conventional.
Diane was known for her bold sexuality and was described as the “ultimate flirt.”
Barry, for his part, also had a complex personal life.
In his memoir Who Knew, he openly reveals that he is gay and had relationships with men throughout his life.
This revelation surprised many, though insiders in Hollywood had long suspected it.
Marriage, Affairs, and an Open Understanding
Diller and von Furstenberg officially married in 2001 after decades of being lovers, friends, and sometimes living apart.
Their marriage was far from typical — Diane had affairs with men, including actor Richard Gere, which caused a decade-long split from Barry.
Barry himself had relationships with men, and both partners maintained a unique and open understanding of their needs.
Diane has proudly described herself as “sexually fluid,” openly admitting to relationships with both men and women.
She has said that Barry “opened to the world” years before his memoir, and that honesty and never lying were the keys to their enduring partnership.
Hollywood Powerhouse and Behind-the-Scenes Influence
Barry Diller’s influence on Hollywood is legendary.
He greenlit classics like The Godfather Part II, Saturday Night Fever, and Raiders of the Lost Ark during his time at Paramount.
Later, he helped create the Fox TV network and played a key role in launching The Simpsons.
Known as “Killer Diller” for his ruthless business style, he was feared and respected in equal measure.
Despite his enormous success, Barry stayed out of the public spotlight for years, partly because he feared the backlash of coming out as gay in an industry not ready for it at the time.
Now 83, he says he’s done hiding, though he remains private about many details of his personal life.
The Couple’s Vibrant Social Life and Modern Adventures
Today, Barry and Diane often travel on his 305-foot sailing yacht, Eos, alongside friends like Amazon founder Jeff Bezos and Lauren Sanchez.
Their social circle is as powerful as their careers, reflecting a lifestyle that blends luxury, influence, and friendship.
Diane’s colorful past includes wild parties at Studio 54, flings with rock stars like Mick Jagger and David Bowie, and candid stories about her sexual adventures.
Yet, she remains grounded in her belief that love and life must be lived with honesty — a philosophy that has clearly shaped her decades-long relationship with Barry.
Facing the Past and Looking Forward
Barry’s decision to come out publicly through his memoir shocked some but felt natural to others who knew him.
His childhood was far from easy, with neglectful parents and a troubled brother, and he suffered a nervous breakdown as a young man.
This background, combined with Hollywood’s pressures, explains much of his lifelong caution about revealing his true self.
Still, Barry insists that his love for Diane has never been in question. “While there have been many men in my life, there has only ever been one woman,” he writes.
Their relationship might not fit traditional molds, but it has lasted for over 50 years — a testament to their passion, honesty, and unshakable bond.
What Remains Behind the Curtain
Even as Barry shares much in his memoir, he keeps certain things close to the chest, refusing to answer probing questions about his personal life.
Known as a demanding boss with a fierce temper, his private nature only adds to the mystique.
Whether he’s been a difficult husband is something only Diane can fully answer.
But what’s clear is that their relationship is far from ordinary — a complicated, passionate partnership that has defied expectations and endured through decades of change.