JFK Jr’s Loves: From Daryl Hannah to Madonna to Carolyn Bessette – All The Women He Romanced

As one of the country's most eligible bachelors — and PEOPLE's 1988 Sexiest Man Alive — JFK Jr.'s love life made headlines. Here's all of his confirmed paramours

Handsome. Charming. Charismatic. Full of Life. John F. Kennedy Jr., the only son of President John F. Kennedy and Jacqueline Kennedy Onassis, was considered one of the most eligible bachelors of his time — and his love life made headlines.

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Now, twenty-five years after his death, a new book,  JFK Jr.: An Intimate Oral Biography by Liz McNeil and RoseMarie Terenzio, based on over 200 interviews with his inner circle and closest friends, reveals new information about his life and loves.

Here’s a look at some of the women who stole his heart.

Related: PEOPLE Named JFK Jr. the Sexiest Man Alive in 1988: Read the Cover Story

Jenny Christian

In his senior year, John fell in love with his Andover classmate Jenny Christian, whom his close friend Sasha Chermayeff calls, “the first love of his life, no doubt.”

“He was impressed by her. Because she was so intelligent and funny,” says Chermayeff of Christian who later went to Harvard.

She remembers Christian typing up a last-minute paper, on Lenin and Trotsky. “She’d sit there for 45 minutes, smoking Larks and then she’d get an A-plus and they would say, ‘Can I keep this to show future students?'"

"[She was] sharp as  a tack,” Chermayeff concluded.

Sally Munro

At Brown University, John fell in love with classmate Sally Munro, whom many say bore a resemblance to his sister, Caroline.

According to John’s friend and Brown classmate Chris Oberbeck who introduced them, “She was a New England, attractive, intelligent girl who came from a big family. She wasn’t trying to be like everybody else.”

John liked her relaxed and warm personality. As Oberbeck put it, “She wore the jeans and the sneakers, not the pleated skirts from New York City.” 

Christina Haag

After graduation, John took up with another Brown classmate, Christina Haag, with whom he shared a passion for theater, and a passionate love affair. They dated for five years and Haag wrote an evocative memoir about their romance, Come To The Edge, in 2011.

They had lived together in a group house at Brown but both were dating other people at the time. After graduation, they began dating while performing in a play together. When John found out she had broken up with a longtime boyfriend after graduation, John’s close friend, Robbie Littell, recalls, “John ran to the window and yelled out ... ’She’s free, the girl I‘m gonna marry!’”

Many friends say the sophisticated Haag was also a favorite of John's mom, Jackie.

Daryl Hannah

After Haag, JFK dated actress Daryl Hannah. He loved her playful side but they had their share of ups and downs.

Amelia Barlow, one of three daughters of John’s close friend, Grateful Dead lyricist John Perry Barlow, had especially warm memories of her.

“I can only tell you what their relationship felt like to me — it felt fantastical, adventurous,” she says, in the book. “It felt somewhat young and a little bit maybe naive or immature compared to his relationship with Carolyn. There was a little bit more, like, fire — and fight.”

Related: Who Is Neil Young's Wife? All About Actress Daryl Hannah

Madonna

In the late '80s, John had a fling with Madonna.  A friend recalls in the book, “She came on to him and it was flattery."

At the time she was still married to Sean Penn, but their relationship was ending. “He loved her body,” says the friend. While the attraction was intense, a friend adds that they never had sex but, adds the friend, “They had fun in other ways.”

Madonna and JFK stayed in touch and years later, he asked her to pose for the cover of his political magazine, George. “John had this idea of having Madonna pose on the cover as his mom,” says Terenzio. “We would dress her in a suit, her signature sunglasses. And a pillbox hat sitting on a stack of books.”

She turned him down via fax saying, in part, “Dear Johnny boy, Thanks for asking me to be your mother, but I’m afraid, I could never do her justice. My eyebrows aren’t thick enough for one…”

Julie Baker

JFK met the model Julie Baker in 1989.

“I had no idea he even liked me or noticed me,” Baker tells the authors. “And less than a week later, he called me up … I was actually surprised to hear from him. He asked if I wanted to go to a poetry reading. And I was like, no. You know, to me that sounded so boring. It didn’t matter that it was John.”

A few days later, he invited her to an Andrew Dice Clay show. “We went and we had a blast,” she says. They dated and remained friends to the end. He had regular lunches with her, right up until the last week of his life.

Related: JFK Jr.'s Close Friends Share Intimate, Never-Before-Told Stories in Revealing Book Excerpt (Exclusive)

Carolyn Bessette

It was Carolyn Bessette, whom JFK met in the early '90s, whom he wooed and married in a storybook wedding on Cumberland Island, Ga. in 1996. They were both seeing other people when they met but as Chermayeff recalls, “He was obsessed from the minute he met her.”

But Carolyn, like Baker, didn’t fall all over him. One friend, Jack Merrill, has fond memories of meeting her for the first time. “John had been telling me about Carolyn,” he recalls. "This is my new girlfriend and I really like her and she’s gonna come by — and then the chair is empty. He was embarrassed and annoyed. I thought it was hysterical … I just loved the fact that she was an hour late … Most girls did not do that to John. She showed up and she sat next to me and we laughed from the minute I first looked at her.”

Related: Were JFK Jr. and Carolyn Bessette-Kennedy Separated When They Died? The Truth About Their Rocky Final Days (Exclusive)

Their tempestuous romance remained so until their last day, July 16, 1999, when she got on the plane he was piloting to Martha’s Vineyard, to first drop off her sister, Lauren, and then fly to Hyannis Port, where they planned to attend his cousin Rory’s wedding the next day.

Says Terenzio, “Neither John, nor Carolyn wanted to end their relationship — their goal was to fix what was broken.”

Related: Carolyn Bessette-Kennedy’s Pals Remember Warm, Silly, Fun-Loving Friend Who Was the ‘Opposite of Buttoned Up’

JFK Jr.: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil is on sale July 16, and available for preorder now, wherever books are sold.

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