A Look Back At JFK Jr. And Carolyn Bessette’s Relationship 20+ Years After Plane Crash

It's hard to believe that it's been so many years since two families were torn apart by tragic loss. John F. Kennedy Jr., the 38-year-old son of former President John F. Kennedy and Jacqueline Kennedy Onassis, 33-year-old wife Carolyn Bessette, and her 34-year-old sister, banker Lauren Bessette, died after JFK Jr.'s plane crashed into the Atlantic Ocean on July 16, 1999.

The shocking moment when the plane was announced to be missing is etched in the memory of many. The next two days saw pieces of the plane and a piece of Lauren's luggage recovered from the Atlantic. It would be three days until substantial wreckage and the bodies of all three were recovered.

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The loss was shocking and heartbreaking to so many who felt attachment to these two families. The Kennedy family had long been marred by an alleged curse that this would become another example of.

From the earliest moments of John F. Kennedy Jr.'s life, the world was fascinated with him. He was born just 17 days after his father was elected president of the United States. For three years, the public watched as he grew up in the White House and then mourned with him as he saluted his father's casket after the president was assassinated.

The public became endeared to JFK Jr. As he grew up, he became one of America's most eligible bachelors and was regularly compared to handsome Hollywood leading men of the time. When he set his sights on Carolyn Bessette, the world took notice.

"They met when he went in for a fitting at Calvin Klein, I believe, and she was the person who dealt with celebrities coming in to get free clothes — I'm sure he paid for his clothes, though," said Carole Radziwill, wife of Kennedy cousin Anthony Radziwill at the time, in the documentary JFK Jr.: The Final Year.

"I think he just liked her, and then they started dating — this was in I'm going to say '92. We were sharing a summer house, Anthony and I and John, and he brought her for Memorial Day weekend. They had been seeing each other for a few months super on the DL [down low]. And that's when I first met her."

It wasn't their moment yet, however. JFK got back together with ex-girlfriend Daryl Hannah. Carolyn focused on her career at Calvin Klein and continued to enjoy her social life as a young professional in New York City until she and John came back together in 1994.

John and Carolyn were married in a very intimate wedding on Cumberland Island, off the coast of Georgia, on September 21, 1996. They instantly became an "it" couple in New York City, causing some issues in their relationship as they were relentlessly hounded by paparazzi.

The couple remained committed to their privacy, even more so as rumors of trouble in their relationship came up. The two were sometimes caught mid-fight around New York City, but they were also caught kissing and making up twice as much.

In 1998, one of Carolyn's sisters, Lauren, moved to the city and joined their social circle. Lauren, along with her twin sister Lisa, was just a year older than Carolyn. Lauren had a fascinating life in her own right as a successful banker with Morgan Stanley who had CEO potential, according to those who knew her.

Lauren moved to New York after spending years working at Morgan Stanley in Hong Kong. There, she was a fixture on the social scene and fluent in Mandarin.

"She would walk into a room and people would think, Okay, somebody brought their assistant. And she'd get up and present the IPO pitch in Mandarin, and people would be like, 'What? I've never seen anything like this,'" friend and former coworker Adam Clammer told Town & Country.

"She was so humble yet so smart and poised."

Once she moved to Manhattan, Lauren became close with Carolyn and John. "Every time I saw them together it was just smiles and laughter and sometimes serious conversation. You could really tell that they were each other’s confidantes in that regard," a source shared.

On that fateful day in 1999, it was rumored Lauren was going to Martha's Vineyard to meet up with Bobby Shriver, whom she was reportedly dating. The plan was to drop her off in Martha's Vineyard before completing their flight to Hyannis Port for Rory Kennedy's wedding. Sadly, none of these plans would come to pass.

Today, people are still just as fascinated with the story of these families than ever before. After 22 years, Carolyn is still hailed a style icon, with Instagram communities dedicated to her "Queen of New York minimalist chic" style.

JFK continues to be remembered as a tragic figure in the Kennedy legacy. He's also the subject of many online conspiracy theories questioning his death despite the overwhelming facts indicating he, Carolyn, and Lauren all perished on impact.