The Captivating Love Story of JFK Jr. and Carolyn Bessette

Multiple accounts detail how the high-profile couple first met and fell in love.

Published on Feb. 16, 2026

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Even nearly 30 years after their tragic deaths, the love story of John F. Kennedy Jr. and Carolyn Bessette continues to fascinate the public. A new FX series, "Love Story," explores their relationship, from their initial courtship to their marriage. While there are varying accounts of how the couple first met, most agree they connected in 1992 and dated for a few years before getting engaged in 1995 and marrying in 1996. Their relationship overcame early obstacles before the couple's lives were cut short in a plane crash in 1999.

Why it matters

The relationship between JFK Jr. and Carolyn Bessette captivated the public's imagination due to their high-profile status and the tragic end to their love story. Revisiting the details of how they met and fell in love provides insight into their dynamic and the challenges they faced as a famous couple.

The details

According to various accounts, JFK Jr. and Carolyn Bessette may have first met in 1992 when Bessette, a Calvin Klein sales associate, was selected to assist Kennedy during a VIP fitting. They later crossed paths at a gala dinner, though Bessette initially assumed Kennedy was there with another woman. The couple eventually reconnected in 1994 and began dating, though Kennedy was reluctant to introduce Bessette to his mother, Jacqueline Kennedy Onassis. After a few breakups, Kennedy proposed in 1995 and the couple married the following year on Cumberland Island, Georgia.

  • In spring 1992, Kennedy booked a fitting at Calvin Klein's VIP room, where Bessette was selected to assist him.
  • In 1994, Kennedy and Bessette reconnected and began dating again.
  • In 1995, Kennedy proposed to Bessette, and she accepted three weeks later.
  • In September 1996, Kennedy and Bessette married on Cumberland Island, Georgia.
  • In 1999, Kennedy and Bessette died in a tragic plane crash.

The players

John F. Kennedy Jr.

The son of former U.S. President John F. Kennedy and Jacqueline Kennedy Onassis, who was known for his high-profile status and relationship with Carolyn Bessette.

Carolyn Bessette

A Calvin Klein sales associate who caught the eye of John F. Kennedy Jr. and became his wife, before their lives were tragically cut short in a 1999 plane crash.

Jacqueline Kennedy Onassis

The mother of John F. Kennedy Jr., who was initially reluctant to meet Carolyn Bessette, his wife.

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What they’re saying

“There's one account of how both were running in Central Park and he was suddenly taken aback by her beauty.”

— Esther Lee, Senior News Editor, The Knot (JFK And Carolyn's Wedding: The Lost Tapes)

“Carolyn was used to guys who were more closed and she had to draw out. John was not that kind of person. If John was interested in you, he was very open and very forthcoming, and she found that to be very refreshing.”

— J. Randy Taraborrelli, Author, "The Kennedy Heirs" (JFK And Carolyn's Wedding: The Lost Tapes)

The takeaway

The captivating love story of JFK Jr. and Carolyn Bessette continues to fascinate the public decades later, highlighting the challenges and triumphs of their high-profile relationship before their tragic end. Their story serves as a poignant reminder of the fragility of life and the enduring power of love.