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While we seem to know anything and everything about John F Kennedy Jr’s marriage to Carolyn Bessette, and all the A-list romances he had beforehand, there’s one we recently heard about: the awful date Brooke Shields had with him.
In a now-resurfaced interview on The Howard Stern Show back in April 2023, the There Was a Little Girl author detailed how she had a huge crush on Kennedy when she was younger, and how she ended up going on a date with him as an adult.
“I was so madly in love with him since the time I was three,” she said, recalling how they met when she was on a skiing trip with her family in Aspen, Colorado. When she tried to impress him with her skiing skills, she nearly toppled over, but it got them talking!
However, soon into talking, he kept saying something, erm, awkward, to say the least, to a woman he was interested in.
“He kept saying I look like his mother,” she said. “Which is really interesting, and a compliment, but it was also like, ‘I don’t know how to feel about this.’ And then we did have a real date.”
So they were interested in one another, and he kept saying she looked like his mom Jackie Kennedy. Yeah, that’s not totally awkward (please sense the sarcasm coming from us, because wow).
Jackie was gorgeous, and Shields is gorgeous; but for JFK Jr. to consistently say they look similar is kinda odd.
Fast forward a bit of time, though, and they went on their first official date. Shields detailed how he took her to a rowdy bar, which they exited in mere minutes of entering. They went back to his hotel, where he tried to make a move on her, which she rejected. He then never reached out to her again, and while Shields was a bit sad afterward, she noted she was happy she could see his “true colors” after one official date.
Before you go, click here to see the best presidential love stories in U.S. history.
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