9 Astonishing Facts About JFK Jr. and Carolyn Bessette’s Love Story

Bassyonni

Published: February 19, 2026 10:15 PM ET

John F. Kennedy Jr. and Carolyn Bessette captivated the world with their love story, which still resonates today. Their romance, marked by glamour and tragedy, has inspired renewed interest through various media, including the recent FX series “Love Story.” Here are some astonishing facts about their relationship that shed light on their connection and life together.

Astonishing Facts About JFK Jr. and Carolyn Bessette’s Love Story

1. How They Met

JFK Jr. and Carolyn Bessette’s love story began with a connection through American fashion designer Calvin Klein. Bessette worked at Klein’s brand as a publicist while JFK Jr. was a high-profile client. Their first encounter reportedly occurred in a dressing room in 1992, thanks to this mutual connection.

2. Left-Handed Love

Interestingly, both JFK Jr. and Bessette were left-handed. This quirky similarity added a unique aspect to their relationship, showcasing their compatibility.

3. The Proposal

JFK Jr. proposed to Bessette while on a fishing boat in Martha’s Vineyard during a Fourth of July trip in 1995. Although she initially declined his proposal, she accepted after three weeks. The engagement ring featured stunning diamonds and sapphires.

4. Absence of Family Connections

One poignant aspect of their story is that Carolyn Bessette never met Jackie Kennedy, JFK Jr.’s mother. Jackie passed away in 1994, before they were introduced. This absence became a source of strain in their relationship.

5. A Mother’s Warning

Before their tragic fate, Bessette’s mother cautioned JFK Jr. about flying with her daughters. Despite this warning, Carolyn and her sister boarded JFK Jr.’s plane, which led to a devastating crash in 1999.

6. Pet Parents

The couple adopted a Canaan dog named Friday.
Bessette also owned a black cat named Ruby, a gift from JFK Jr.

7. Dining Preferences

Instead of luxury dining, JFK Jr. and Bessette preferred quaint local spots near their Tribeca home. Their favorite eateries included The Odeon and Bubby’s, where they enjoyed casual meals.

8. An Intimate Wedding

Their wedding took place in 1996 on Cumberland Island, Georgia. The ceremony was intimate, held in a chapel without electricity, illuminated solely by candlelight, creating a romantic atmosphere.

9. Tragic Flight

JFK Jr. had earned his private pilot’s license and had accumulated 310 hours of flight time before the fatal flight. Tragically, he chose to fly alone on a night when a flight instructor had intended to accompany him. The crash resulted from spatial disorientation, leading to national mourning.

The love story of JFK Jr. and Carolyn Bessette continues to intrigue many, serving as a reminder of both the beauty and the fragility of life. Their remarkable bond and the circumstances surrounding their lives leave a lasting impression on American culture.