Howard Stern Hints At Private Connection To Carolyn Bessette But Won’t Share Details

Howard Stern shares he knew the "real" Carolyn Bessette but remains vague about how they met, sparking curiosity among fans. The Howard Stern Hints At Private Connection To Carolyn Bessette But Won’t Share Details first appeared on The Blast

Broadcaster and media personality Howard Stern opened up about his memories of Carolyn Bessette, offering a glimpse of their past interactions. While he was vague on specifics, his reflections revealed a personal connection that has fans curious. The host also recalled meeting Bessette’s husband, John F. Kennedy Jr., and the time he was asked to appear on the cover of “George” magazine.

Stern’s comments come amid the airing of “Love Story: John F. Kennedy Jr. & Carolyn Bessette,” a limited series focused on the late couple’s relationship.

Howard Stern Said He Knew The ‘Real’ Carolyn Bessette

In an episode of “The Howard Stern Show,” the host talked about his interactions with Bessette, describing her as a “lovely” woman. “I knew the real Carolyn Bessette,” he noted, but admitted that he couldn’t say he knew her very well.

However, Stern had enough interactions with the fashion publicist to form an opinion about her. “We had many, many conversations, more than casual conversations,” he shared, adding, “I don’t want to go into how I knew her, but I knew her. I know enough to keep my mouth shut about that. Some stuff you do have to keep private.”

Despite his cryptic statements, Stern said Bessette was “very nice, very open, and talkative” with him and wasn’t snobbish or arrogant. “I don’t have any juicy, gossipy story,” he added.

Howard Stern Posed For JFK Jr’s Magazine

Stern also recalled the time he agreed to pose for JFK Jr.’s “George” magazine, which fused politics with pop culture. The publication was famous for its covers, which featured celebrities dressed as historical figures.

The host said that he rarely did magazine cover shoots at that time, but he couldn’t say no to JFK Jr. as he was “American royalty” and “the nicest guy in the world.” Stern admitted that he also did it in the off-chance that JFK Jr. would agree to be on his show.

Stern said JFK Jr. was present during the shoot, and they had him dressed as George Washington holding a chainsaw and chopping down a cherry tree. “I was supposed to be George Washington, but George Washington didn’t wear this sh-t I was wearing. I looked like Paul Revere in drag,” he said. Admittedly, Stern said it was one of the “worst covers” he ever did.

John F. Kennedy Was A Guest On The Host’s Show

JFK Jr. returned the favor and agreed to be interviewed by Stern. It was a bold move, as the host was known for his provocative style of interviewing. RoseMarie Terenzio, JFK Jr.’s personal assistant, wrote about that time in her 2012 book, sharing how she and Bessette were anxious about the interview. “I was really nervous. Howard had an unmatched ability to make people look stupid,” she wrote.

Stern was able to get some interesting facts about him, such as losing his virginity in high school, and he also asked about his fight with Bessette in Washington Square Park that was captured by paparazzi. JFK Jr. explained, saying it was a “silly argument” that was blown out of proportion by the media. Ultimately, JFK Jr. completed the interview unscathed.

Howard Stern’s Thoughts About The Show

Stern said that he’s been watching “Love Story,” and he shared his take on the controversial series. The host said that he agrees with actress Daryl Hannah regarding how she was portrayed. The actress dated JFK Jr. before he got together with Bessette, and her relationship with him was included in the show.

As The Blast previously reported, Hannah wrote an essay calling out the show for adding scenes that never happened in real life and for portraying her in a bad light. “She’s right. Her complaint is they’re making her look like a douche. From everyone I know who knows Daryl Hannah, they say she’s a great girl,” Stern said. Apart from that, Stern said he and his wife “love the TV show.”

The Kennedy Family Blasted ‘Love Story’

JFK Jr.’s nephew, Jack Schlossberg, has repeatedly spoken out about “Love Story,” accusing producer Ryan Murphy of profiting from tragedy. “The guy knows nothing about what he’s talking about, and he’s making a ton of money on a grotesque display of someone else’s life,” Shclossberg said.

In July 2025, Murphy said the series was based on the book “Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy,” which he noted was “sympathetic to both people.” Admittedly, he didn’t expect backlash from the Kennedys.

“Love Story” premiered on FX and Hulu in February, and the ninth and final episode will air on March 26.

The Howard Stern Hints At Private Connection To Carolyn Bessette But Won’t Share Details first appeared on The Blast