John F. Kennedy Jr. & Carolyn Bessette's Relationship Didn't Have a Fairytale Beginning

  • Oops!
    Something went wrong.
    Please try again later.

If you purchase an independently reviewed product or service through a link on our website, SheKnows may receive an affiliate commission.

John F. Kennedy’s romance with Carolyn Bessette has always been viewed as a fairytale with a tragic ending. However, an upcoming book, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller, reveals that their love wasn’t easy from the get-go — there were always challenges surrounding the relationship.

More from SheKnows

In an excerpt obtained by People, it’s clear that they were “smitten” from the start, but their unestablished dating rules caused quite a bit of chaos. After meeting at a 1992 fitting at Calvin Klein, where Bessette worked, JFK Jr. invited her to a gala dinner. “Sitting next to him was another woman that Carolyn either mistook as his date or actually was his date,” wrote Beller. That situation was soon forgotten as the spring season was filled with “a haze of sultry dinners, dancing, and walks in Central Park.” She even joined JFK Jr. at his summer share in Long Island with his cousin, Anthony Radziwill. Things were absolutely dreamy until a major fight ensued over a letter that the former president’s son received.

Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller.
Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller.

Buy Now $26.99

The note was from a friend of JFK Jr.’s and shockingly “claimed Carolyn was a user, a partier, that she was out for fame and fortune [and] ‘dated guys around town.'” He reportedly stormed out of their dinner in a huff. And of course, there was his very active and public dating life with other women. “John, meanwhile, had been spotted about town with Daryl Hannah that fall—all documented in the press,” the excerpt read. “Granted, Carolyn knew she wasn’t his only option. When she came across a pair of [former girlfriend] Julie Baker’s duck boots in John’s apartment, despite them being a size too small, she made a point of wearing them.”

Bessette often played petty dating games to make her on-again, off-again boyfriend jealous — and it worked. “John called all the time,” a Bessette friend revealed in the book, “[We recorded] an outgoing message on her answering machine.” Anyone who called would get Carolyn saying, “Hey, hon, I’ll be back by seven o’clock, can’t wait to see you!” The idea was that John would hear it and assume she’d moved on. John did—and he called even more.” But by July 4, 1995, the couple had worked out their issues and officially got engaged. 

Beller’s book echoes what other authors have covered in the past — JFK Jr. and Bessette were incredibly glamorous together, but their relationship was hard. “John and Carolyn loved each other,” J. Randy Taraborrelli, author of The Kennedy Heirs told People in 2019. “but their struggles were much more real than people realize.” From the outside, their life looked like a dream come true, but the truth was that JFK Jr. and Bessette were like any ordinary couple trying to find their place together, except the whole world was watching.

Before you go, click here to see photos of JFK and Jackie O.’s grown-up grandkids.

John Schlossberg, Caroline Kennedy, Tatiana Schlossberg
John Schlossberg, Caroline Kennedy, Tatiana Schlossberg

Best of SheKnows

Sign up for SheKnows' Newsletter. For the latest news, follow us on Facebook, Twitter, and Instagram.