How JFK Jr. Challenged Himself to Become a 'Good Man' – and Step Out from His Father's Shadow

One of John F. Kennedy Jr.'s closest friends reveals how the late icon differentiated himself from his father when it came to women

Photo: Brownie Harris/Corbis/Getty

Editor’s note: On Thursday night ABC aired the new documentary special The Last Days of JFK Jr. The below story was first published on July 21, 2016.

While close friends say John F. Kennedy Jr. was not one to directly address his father’s infidelity, one confidante believes it’s one of the reasons the young Kennedy focused on becoming a consistent and loyal partner.

In I Am JFK Jr., a new SPIKE TV documentary to air Aug. 1 and featured in this week’s PEOPLE, close friend John Perry Barlow, a Wyoming rancher and Grateful Dead lyricist, recounts a conversation they had when John was at Brown University.

“He called me once and said, ‘It seems like it would be a cakewalk for me because everyone expects me to a great man. But it does seem to me, as I read these biographies of great men through history, they were not particularly great at home. Even my father was no model – and I think it would be a much more interesting challenge to see if I could make myself into a good man.’ ” Barlow recalls.

As for the specifics of what John was referring to, Barlow says it’s open to interpretation: “I think he was kind of talking about infidelity, about how his father had been kind of a ladies’ man, which despite widespread belief, John never really was.”

While JFK Jr. was considered perhaps the world’s most eligible bachelor, he was also known for being a committed boyfriend to his various girlfriends over the years.

“He was kind of a monogamous guy,” says Barlow. Still, he adds with a laugh, “sometimes the turnover was a little high.”

But John’s faithfulness was more than just a reaction to his father, says Barlow: “I also think he had a natural instinct for not hurting people’s hearts.”

Two weeks before his death in a plane crash on July 16, 1999, alongside wife Carolyn Bessette Kennedy and sister-in-law Lauren Bessette, JFK Jr. and Barlow revisited that long ago conversation.

“At one point, I said ‘Do you remember that conversation we had when you were in college about you becoming a good man?’ ” Barlow recounts. “He said ‘Of course I do. I think about that conversation frequently,’ ” Barlow recalls him saying.

Barlow says he then told him, “you’ve become that person I aspired that you would be. You’ve been graceful and kind and good.”

After a long pause, John responded: “I am very proud you are proud of me.”

It’s only one of the surprising revelations about John that make up I Am JFK Jr., which also opens in select theaters this week.

Says the film’s director, Derik Murray, “With John, we didn’t know what to expect, but what was consistent was that he was a man who cared about people, a man that had ambitions of his own, as opposed to just riding the jet stream of his family.

“This notion that he was poised and set up for greatness, he thought about it but he would rather have been a good man,” Murray adds. “That’s not something that’s echoed today in what we read about our current pop culture icons – and it made him unique.”

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