“I know enough to keep my mouth shut about that,” Stern said of his connection to one half of the “Love Story” couple.

Howard Stern talks private friendship with Carolyn Bessette, recalls cover shoot for JFK Jr.’s magazine: ‘I looked like Paul Revere in drag’

"I know enough to keep my mouth shut about that," Stern said of his connection to one half of the "Love Story" couple.

By Marina Watts

Marina Watts

Marina Watts is a news writer for with seven years experience covering entertainment, pop culture and celebrity news. Her previous work appears in PEOPLE, Bustle and Newsweek.

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March 24, 2026 12:31 p.m. ET

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Howard Stern; John F Kennedy Jr. Credit:

- Howard Stern opened up about his relationship with John F. Kennedy Jr. and Carolyn Bessette

- The radio personality called JFK, Jr. a "super nice guy" and claims he knew "the real Carolyn."

- He wouldn't divulge *how *he knew Bessette, however: "I know enough to keep my mouth shut about that."

Howard Stern is one of the many people keeping up with FX's *Love Story: John F. Kennedy & Carolyn Bessette*, and he's sharing insight into his real-life connection to the couple.

Returning to *The Howard Stern Show *after a hiatus, the radio personality opened up about his friendship with Carolyn Bessette, whose romance with John F. Kennedy Jr. is dramatized in the limited series, which wraps up this Thursday.

"I knew the real Carolyn Bessette,” he said. “I won't say I knew her well, but we had many, many conversations, more than casual conversations. She was very lovely. She was like a really nice woman."

Stern said he wouldn't elaborate on how exactly he knew Bessette, however. "I know enough to keep my mouth shut about that. Some stuff you do have to keep private … But she was very nice to me, very open and talkative. She didn't give me the nose-up-in-the air kind of thing. I don't have any juicy, gossipy story.”

John F. Kennedy, Jr. and Carolyn Bessette Kennedy in Boston in May 1999.

Justin Ide/Newsmakers via Getty

Stern also reminisced about posing for the cover of JFK Jr.'s *George *magazine, highlighting Kennedy's attention to detail and involvement with the April/May 1996 issue. “He actually showed up to the shoot,” Stern recalled.

“It's one of the worst covers I ever did, and I did a lot of bad ones," Stern said of the photo, which ran alongside the headline "What's so good about virtue?" "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 s--- I was wearing. I looked like Paul Revere in drag.”

Howard Stern on the cover of 'George Magazine'.

George Magazine

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Despite Stern's doubt, Kennedy and the photographer gave him the supermodel treatment. "They go, 'Gorgeous, you look great. This is the greatest cover,'" he said, adding that the shoot occurred before he knew he could ask to approve a photo before it hit newsstands.

"I guess I kind of look like Captain Hook or something," Stern quipped. The radio personality concluded he was wary of doing magazine covers, but when Kennedy asked, he was happy to oblige. "He was a super nice guy."

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*Love Story** *stars Paul Anthony Kelly as Kennedy and Sarah Pidgeon as Bessette. Their costar Constance Zimmer told Decider that the final episode will be "very, very difficult for everybody to watch." "I think we all know what's coming," Zimmer said. "It's just how we're telling it."

Kennedy and Bessette married in 1996. Their lives were cut short in July 1999 when they, along with Carolyn's sister Lauren, died in a plane crash off the coast of Martha's Vineyard. Their bodies were recovered days later and it was determined that they died on impact.

Carolyn Bessette and John F Kennedy, Jr. in New York in 1997.

Ron Galella Collection via Getty

The finale of *Love Story: John F. Kennedy Jr. & Carolyn Bessette* will air on Thursday, March 26 on FX, and be available to stream on Hulu the following day.

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