Fans of 'Love Story' on FX Want to Know About Carolyn Bessette's Boyfriends

Carolyn, John F. Kennedy Jr., and her sister, Lauren, died in a plane crash in 1999.

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Published Feb. 27 2026, 3:56 p.m. ET

Who Were Carolyn Bessette's Boyfriends Before JFK, Jr.?
Source: Mega

The Kennedy and Bessette families were devastated when John F. Kennedy, Jr., his wife, Carolyn Bessette Kennedy, and her sister, Lauren Bessette, died after the plane he was piloting crashed on July 16, 1999. Their love story is the subject of the limited series on FX, Love Story: John F. Kennedy Jr. & Carolyn Bessette, and fans are curious about her past relationships before she married John-John.

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Kennedy was under a microscope for his entire life, being the son of President John F. Kennedy, who was assassinated in 1963. The paparazzi chased him everywhere, and especially during his long-time relationship with actor Daryl Hannah. After their breakup, he married Carolyn, and she was thrust into his famous life, which included dealing with the paparazzi. The Calvin Klein executive became as popular as her husband, and fans want to know about her boyfriends before she was a Kennedy.

Carolyn Bessette Kennedy and John F. Kennedy, Jr., in 1999.
Source: Mega
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Who were Carolyn Bessette's boyfriends before JFK, Jr.?

According to People, Carolyn dated a Calvin Klein model before she began dating John. Carolyn's boyfriend was model Michael Bergin, who was the Calvin Klein underwear model after Mark Wahlberg's successful and infamous Calvin campaign. Carolyn had reportedly begun dating Michael during a breakup with John after he'd been sent a letter claiming she was only dating him for fame.

Michael is also an actor who once dated Kate Moss, and he starred on Baywatch from 1997 to 2001, per IMDb. The model also had guest-starring roles on CSI: Miami, Charmed, Central Booking, and The Wrong Valentine. He wrote a book back in 2004 about this relationship with Carolyn, The Other Man: John F. Kennedy Jr., Carolyn Bessette and Me.

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Not much is known publicly about Carolyn's boyfriends before John and Michael.

According to People, John proposed to Carolyn Bessette while on a fishing boat off the coast of Martha's Vineyard one weekend back in July 1995.

"He went into this thing about how everything's better with a partner, not just fishing but life," said his former assistant. "He said, 'I want you to be my partner.'"

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Carolyn reportedly made John wait for an answer for three weeks before agreeing to be his wife. The couple was married in a secret ceremony on Sept. 21, 1996, on Cumberland Island in Georgia, and they reportedly had a passionate relationship.

"They would love hard, and fight hard," said a friend of the couple's to the outlet. "But they were very much in love."

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Former Real Housewives of New York star Carole Radziwill was good friend of the couple, and she called Carolyn "quite a loveable person."

"She was clever, she was naughty, and she had that balance of being able to be really serious and deep yet funny," she added.

The couple died after his plane crashed into the sea on the way to Cape Cod for the wedding of his cousin, Rory Kennedy. Lauren, John, and Carolyn were the only three on board, and they were killed when the plane crashed into the dark water near Martha's Vineyard.

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