Inside Carolyn Bessette's Dating History: From Michael Bergin to John F. Kennedy Jr.

Samantha StutsmanSat, February 28, 2026 at 11:30 AM UTC

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John F. Kennedy Jr. and Carolyn Bessette; Michael Bergin.Credit: Ron Galella/Ron Galella Collection via Getty; Jim Smeal/Ron Galella Collection via Getty -

Carolyn Bessette dated Calvin Klein model, Michael Bergin, before marrying John F. Kennedy Jr.

Bessette and JFK Jr. wed in 1996

The couple's famed romance is depicted in FX's Love Story

Before she married John F. Kennedy Jr., Carolyn Bessette was living a private life in New York City and building a career at Calvin Klein.

Though she had dated before — most notably being linked to model Michael Bergin in the early '90s — none of her previous relationships attracted the intense scrutiny that would later define her life. JFK Jr. and Bessette met in 1992, and according to friends, he was immediately captivated.

“[Bessette] intrigued him more than anyone he’d ever met. A force of nature. He said he wanted to marry her. He was adamant,” his close friend Robbie Littell said in Liz McNeil and RoseMarie Terenzio's book, JFK Jr.: An Intimate Oral Biography.

The pair went on to marry in a secret ceremony on Georgia’s Cumberland Island on Sept. 21, 1996. Tragically, on July 16, 1999, JFK Jr. was piloting a small plane to Martha’s Vineyard when it crashed. He died, as did his passengers: Bessette and her sister, Lauren.

JFK Jr. and Bessette's romance has continued to fascinate the public decades later, and it's dramatized in FX’s Love Story, which premiered on Feb. 12.

Here's everything to know about Carolyn Bessette's dating history.

John Cullen

Carolyn Bessette; John Cullen.Credit: Richard Corkery/NY Daily News Archive via Getty; Graig Abel/Getty

Bessette and John Cullen briefly dated while they both attended Boston University, according to Vanity Fair and CBS News. He was on the school's hockey team and eventually played in the NHL.

Michael Bergin

Carolyn Bessette; Michael Bergin.Credit: Trevor Gillespie/Getty; Ron Galella, Ltd./Ron Galella Collection via Getty

In the early '90s, Bessette dated Bergin while she was working at Calvin Klein. His career started in earnest when he secured a role in the brand’s high-profile 1994 underwear campaign alongside Kate Moss.

Bergin later reflected on their relationship in his 2004 memoir, The Other Man: John F. Kennedy Jr., Carolyn Bessette, and Me, offering his personal account of their time together.

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In the book, Bergin described their romance as significant. “Carolyn and I had a very intense love for each other," Bergin told famed author Edward Klein in 2003, per Vanity Fair. "We were inseparable for a couple of years. And I know deep in my heart that she still loved me even after she married John Kennedy. Some things just don’t end.”

John F. Kennedy Jr.

Carolyn Bessette and John F. Kennedy Jr. in 1996.Credit: Stephane Cardinale/Sygma via Getty

Bessette and JFK Jr. first met in 1992 when she was working at Calvin Klein, and he was launching George magazine. They began dating quietly, but once their relationship became public, it quickly drew tabloid attention.

On Sept. 21, 1996, they married in a highly private ceremony on Georgia's Cumberland Island. The wedding was kept secret until after it took place — a deliberate move to avoid media frenzy.

They settled into married life in N.Y.C., though life in the public eye proved relentless. By the spring of 1999, Bessette and JFK Jr. had begun marriage counseling. Still, friends later insisted their relationship was not beyond repair.

Carole Radziwill, who was married to JFK Jr.'s cousin Anthony Radziwill, told PEOPLE in June 2017 that the couple weren’t as troubled as rumors suggested. “To say their marriage was on the rocks is just inaccurate,” she said.

The Kennedy Heirs author J. Randy Taraborelli echoed that sentiment, adding, “They were working on their relationship at the time they died. They thought they had all the time in the world to figure this out.”

On July 16, 1999, JFK Jr. was piloting a small plane to Martha’s Vineyard when it crashed off the coast of Massachusetts, killing him, Bessette and her sister, Lauren.

For more on the lives of John F. Kennedy Jr and Carolyn Bessette Kennedy, pick up PEOPLE's special edition, available now on newsstand and here [https://a.co/d/00gpN1dE]

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Source: “AOL Entertainment”