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Brooke Shields Rejected John F. Kennedy Jr and Said He Was ‘Less Than Chivalrous’ About It

Samantha Franco
Photo Credit: Robin Platzer / IMAGES / Getty Images and Ron Galella / Ron Galella Collection / Getty Images
Photo Credit: Robin Platzer / IMAGES / Getty Images and Ron Galella / Ron Galella Collection / Getty Images

Brooke Shields appeared on The Howard Stern Show to discuss her new documentary, Pretty Baby: Brooke Shields. During the interview, she discussed a memory from her past involving a short-lived romance with John F. Kennedy Jr. She revealed that he wasn’t exactly the most chivalrous person, especially after she said no to going all the way with him on their first date.

Shields had a crush on Kennedy for a long time

John F. Kennedy Jr. shirtless on a beach.
John F. Kennedy Jr. during the ‘Kennedy Family Labor Day Weekend in Hyannis Port’ on August 31, 1980, at Kennedy Compound Pier in Hyannis Port, Massachusetts, United States. (Photo Credit: Ron Galella / Ron Galella Collection / Getty Images)

During the interview, Shields revealed that she’d had a crush on John F. Kennedy Jr. for a long time. He was five years older than she was, but she said, “I was so madly in love with him since the time I was three. My mom would say, ‘That’s the boy you’re going to marry,'” she explained.

As luck would have it, in the 1980s Shields and her mother took a trip to Aspen, Colorado to attend a wedding at the same time the Kennedy family was visiting for a skiing vacation. Shields’ path was finally going to cross with that of her longtime crush, and she wasn’t going to let the opportunity go to waste.

Despite the fact that she had “never skied before in [her] life,” Shields tried to impress Kennedy with her non-existent skills on the slopes. Somehow, it worked.

She felt she was falling in love

Headshot of Brooke Shields from the 1980s.
A headshot of Brooke Shields, circa 1982. Taken in New York City. (Photo Credit: Robin Platzer / IMAGES / Getty Images)

One way or another, Shields managed to catch Kennedy’s attention, and she was invited to join the family for an outing to a local bar. In Shields’ opinion, the place was a bit too hectic. It’s a little surprising to think that the prominent political Kennedy family would have gone somewhere like that.

When she described the scene, Shields said, “everyone was just drinking at the bar and there were bar fights.” Kennedy must have either sensed her discomfort or wanted the night to progress, as he asked if she wanted to go. “He was like, ‘Do you want to get out of here?’ And I was like, ‘Uh, yeah, I do want to get out of here, John Kennedy,'” Shields said.

Shields called him “down-to-earth and funny and irreverent,” but the next portion of their night, what she called their “real date,” didn’t end the way Kennedy would’ve liked. The two shared a passionate kiss, one that Shields described as “the best kiss I’ve ever had in my life.” However, when Kennedy put going further on the table, she “froze.” She said it was because he was “so precious to me.”

Ultimately, Shields turned down his offer, saying it was “because I kind of loved him too much.”

She believes he showed his true colors

Headshot of John F. Kennedy Jr, his head tilted downward slightly.
John F. Kennedy Jr. enjoys the Hollywood nightlife circa 1981 in Los Angeles, California. (Photo Credit: Michael Ochs Archives / Getty Images)

Shields explained her thought process before she made the decision to turn the crush of her life down. “I was like, ‘Oh my God, you’re falling in love and if you sleep with him, he may not talk to you again and you can’t handle that.'” For her, it meant a lot more than it probably would have to him.

“I wasn’t playing a game, I really was just so afraid of being really hurt because if I slept with him I would have given him my entire universe, my heart, my everything,” she explained. Not long after she rejected him, Kennedy sent her on her way.

“I had to get a cab home, which was a little less chivalrous, in my opinion,” she remarked. Then, quite immaturely, Kennedy ignored her the following day. “He didn’t look at me and he didn’t talk to me,” she explained. “On the one hand, I was like ‘[expletive].’ On the other hand, I was like, ‘Oh, thank God, because he still might not have talked to you.”

In the end, she realized that she had made the right decision for herself and was happy she chose not to give him more than a kiss that night. “He showed his true colors in that,” she explained.

More from us: 13 Celebrity Couples Who Make Us Believe in True Love

Kennedy eventually went on to wed Carolyn Bessette-Kennedy in 1996. The two were tragically killed in a plane crash in 1999 with Kennedy at the helm.

Samantha Franco

Samantha Franco is a Freelance Content Writer who received her Bachelor of Arts degree in history from the University of Guelph, and her Master of Arts degree in history from the University of Western Ontario. Her research focused on Victorian, medical, and epidemiological history with a focus on childhood diseases. Stepping away from her academic career, Samantha previously worked as a Heritage Researcher and now writes content for multiple sites covering an array of historical topics.

In her spare time, Samantha enjoys reading, knitting, and hanging out with her dog, Chowder!