Howard Stern Teases that He Knew the ‘Real’ Carolyn Bessette, Says They Had ‘More Than Casual’ Conversations

Published: Mar 25 2026

Howard Stern recently reminisced about his friendship with Carolyn Bessette, but didn't reveal all the intimate details. "I knew the genuine Carolyn Bessette," the 72-year-old radio personality insisted during an episode of The Howard Stern Show on March 23rd, as reported by Rolling Stone. "I won't say I knew her intimately, but we had numerous conversations, far beyond casual ones. She was truly delightful. She was like a wonderfully kind woman."

"I don't want to delve into how I met her, but I did know her. I know enough to keep my lips sealed about that," Stern continued. "Some things you just have to keep private... But she was very kind to me, very open and talkative. She didn't give me the cold shoulder. I don't have any juicy, gossip-worthy stories."

Howard Stern Teases that He Knew the ‘Real’ Carolyn Bessette, Says They Had ‘More Than Casual’ Conversations 1

While the comedian chose not to share the origins of their meeting, he also spoke about posing for the April 1996 cover of George, John F. Kennedy Jr.'s magazine. "He actually showed up to the shoot. It's one of the worst covers I ever did, and I've done a lot of bad ones," Stern recalled. "They convinced me to be chopping down a cherry tree with a chainsaw dressed up in colonel garb. I guess I was supposed to be George Washington, but George Washington didn't wear this ridiculous stuff I was wearing. I looked like Paul Revere in drag."

"John and the photographer did that thing they do to supermodels. They go, 'Gorgeous, you look great. This is the greatest cover,'" Stern recounted. "I'm posing while the guy is clicking away, and I'm posing like I'm Cindy Crawford or one of the Hadid sisters. That was before I knew about photo approval. I guess I kind of look like Captain Hook or something."

The famed broadcaster said he didn't necessarily want to be on magazine covers, but did it for JFK Jr., who, in turn, came on his radio show. "I would do Rolling Stone and that was the only one," Stern admitted. "But when John Kennedy Jr. [asks], who is literally American royalty and the nicest guy in the world... he was a super nice guy. And there was the opportunity that perhaps he'd come on the show."

When JFK Jr. appeared on Stern's show, he discussed his now-infamous public fight with Bessette in an NYC park, calling it "a silly argument," according to People.

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