John F. Kennedy Jr.’s Girlfriends: Who Did He Date?

Getty John F. Kennedy Jr. had many girlfriends but only one wife - Carolyn Bessette.

First let’s start with the woman he married: Carolyn Bessette-Kennedy. She died with him in a plane crash off Martha’s Vineyard in 1999, along with her sister, Lauren Bessette. However, before he settled down with Carolyn for the three short years their marriage had, John had relationships with some of America’s most famous women, from Madonna to Daryl Hannah. You can read more about his girlfriends later in this article.

“I think John always was attracted to women who were a little challenging to him,” fraternity brother Richard Wiese told ABC. “The worst thing, as a woman, you could have been, was to yes him to death.”

The president’s son – with his movie star looks and his affable personality – had plenty of relationships during his 38 years, but several of them were long term. One friend joked that John was “sleeping with every hot chick on the planet,” according to The New York Daily News.

“Biography: JFK Jr—The Final Year” will run on Tuesday, July 16, 2019 at 9 p.m. ET on A&E Network. “July 16, 2019 marks the 20-year anniversary of John F. Kennedy Jr.’s death. This two-hour documentary special, airing on the anniversary, reframes the last year of his life in an entirely new way,” A&E wrote in a statement.

Here’s what you need to know:

Marriage to a Style Icon


Carolyn Bessette-Kennedy and JFK Jr.

Carolyn Bessette, a publicist at Calvin Klein, was a style icon, and many people saw similarities between Carolyn and John F. Kennedy Jr.’s mother, Jacqueline Kennedy Onassis. Both were elegant, regal in a sense, mysterious and they had a similar mystique that would have been at odds with today’s media age: Both were hesitant to engage with the press. Their fashion sense was iconic, streamlined, and trailblazing.

john f. kennedy jr.

John F. Kennedy Jr. and Carolyn Bessette.

The couple was married three years before the plane crash, in 1996, on tiny Cumberland Island in Georgia. You can see photographs of them here.

According to Southern Living, the ceremony was held in the “tiny First African Baptist Church, filling the church’s eight pews with family and friends and no media. They held the reception at the historic Greyfield Inn, the lone hotel on the secluded island, some 20 miles off the coast of Georgia.” No one knew outside those invited until after the wedding was over.

However, toward the end of their lives, there were many rumors of tribulations and strife in the marriage, with some reports even saying they were living apart toward the end. Other friends said that Carolyn was simply having great difficulty dealing with the glare of fame.

Here are some of the girlfriends of John F. Kennedy Jr.:


Billboard Women in Music 2016 Red Carpet, Billboard Women in Music 2016 Red Carpet pics, Billboard Women in Music 2016 Celebrities, Billboard Women in Music 2016 women who attended, Billboard Women in Music 2016 pics

Madonna attends the Billboard Women in Music 2016 event on December 9, 2016 in New York City.

They may seem like a completely odd couple in retrospect, but it’s true that John F. Kennedy Jr. once dated Madonna. At least that’s according to the book The Good Son: JFK Jr. and the Mother he Loved by Christopher Anderson,.

The book alleged, according to Irish Central, that, in 1988, “the same year JFK Jr. was named the Sexiest Man Alive by People magazine, he and the Material Girl began a steamy affair.”

The article reports that JFK Jr. was still with his long-time girlfriend Christina Haag, and Sean Penn and Madonna had only recently split up.

“The only place the superstar couple could let their guard down was in Hyannis Port, where they bundled up in sweaters and jackets and jogged on the beach. Inside the compound, they curled up by the fire, sipping daiquiris from Waterford crystal glasses,” the book claimed. However, Jackie put the kibosh on the romance, according to Irish Central, reportedly because she didn’t like Madonna’s image and, perhaps, how she tried to channel Marilyn Monroe.

Christina Haag

Christina Haag was John F. Kennedy Jr.’s college girlfriend, and their relationship lasted for a number of years. She eventually wrote a memoir about their relationship.

In one excerpt from the memoir, she recalled, “We were together for the next five and a half years, as he studied law at N.Y.U. and began at the Manhattan D.A.’s office, and I performed in plays and acted in television and independent films. Our apartments were blocks away from each other on the Upper West Side, we spent weekends at his mother’s houses in New Jersey, Martha’s Vineyard, and Hyannis Port, and during the summers of 1987 and 1988, we lived together in Washington, D.C., and Venice, California. We also loved to travel. And in the early spring of 1989, we took a trip to a place neither of us had been before—Treasure Beach, on the remote southern coast of Jamaica.”

However, the relationship wasn’t to last. The relationship lasted five years.

Christina Haag has developed a career in acting, performing in theaters throughout the United States, according to IMDB, and working “in film and television, with leading roles in movies of the week and on shows such as E.R., Providence, Family Law, Heroes, Boston Public and Law and Order.”

Daryl Hannah

daryl hannah boyfriend

JFK Jr. and Daryl Hannah

The movie star Daryl Hannah and John F. Kennedy Jr. were in a serious relationship and, in retrospect, she resembled his eventual wife.

According to People Magazine, their relationship also lasted five years. They met “in the early 1980s when both were vacationing in St. Martin in the Caribbean with their families, then locked looks again at the 1988 wedding of his aunt Lee Radziwill to director Herb Ross, who had worked with Hannah in Steel Magnolias,” People reported.

By 1994, the couple had split up, though.

Julie Baker

Julie Baker was a model who has confirmed she also dated John F. Kennedy Jr. According to Town and Country Magazine, they had a relationship that lasted two years and she thought he was quirky and adventurous.

“I just loved that he was kind of silly, quirky, forgetful, fun, and adventurous,” Baker said in a new ABC documentary on JFK Jr.

Sarah Jessica Parker

Sarah Jessica Parker son

GettySarah Jessica Parker

Yes, says the new ABC documentary, JFK Jr. also dated actress Sarah Jessica Parker. She has confirmed as much. She told Andy Cohen of JFK Jr.: “He had exquisite hair, it was like a paintbrush, do you know what I mean?”

She also described kissing him as “pleasant.” She wouldn’t say much more, telling Cohen, “I feel like we’ve covered this territory, like if he were alive I’d feel more comfortable, if he were accomplishing all the things that I’m certain he was going to accomplish, and living a really joyful and adventurous life then I would probably feel more comfortable answering more questions about him.”

One report said that Sarah Jessica Parker met JFK Jr. at an airport wearing only a mink coat, but she denied the story.

Read More