Fact vs. Fiction in Love Story: John F. Kennedy Jr. & Carolyn Bessette

Carolyn Bessette Impresses Calvin Klein With Her Style Suggestions for Annette Bening

In Love Story: John F. Kennedy Jr. & Carolyn Bessette, Carolyn (Sarah Pidgeon) suggests that Annette Bening (Megan Channell) wear a Calvin Klein suit to the Bugsy premiere, rather than the dress the designer himself selected for the actress.

While it's unclear whether she styled that particular look for the future Mrs. Warren Beatty, according to a 1996 New York Times article, Carolyn was the go-to saleswoman for Calvin Klein's celebrity clientele, including Annette, Diane Sawyer and Blaire Trump.

"She would guide them through the collection, tell them what looked good on them, and advise them on how to put it all together," Paul Wilmott, then Calvin Klein's VP of public relations, told the paper. "It was a wonderful thing. She sold millions of dollars of clothes over a period of time."

Another Love Story scene illustrating Carolyn's savvy has the eventual PR director encouraging Calvin (Alessandro Nivola) to hire Kate Moss for a campaign.

And Carolyn really was an early champion of Moss, who helped define the Calvin Klein brand in the 1990s. 

Carolyn and John First Lay Eyes on Each Other at a Gala  

As it unfolds in Love Story, Calvin introduces Carolyn and John at a charity gala in 1992 and sparks fly, though Carolyn refuses to give him her phone number, pointing out he knows where he works.

"He was just bored," Carolyn tells her friends at a nightclub afterward as her sometimes-lover Michael Bergin (Noah Fearnley)—dubbed "sexy doorman" by her pals—walks in.

Soon enough, John shows up unexpectedly at Calvin Klein and asks for a private fitting with Carolyn. He asks her to dinner and, once he leaves, her colleagues go nuts.

In reality, according to Elizabeth Beller's 2024 book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, they first met in the spring of 1992 when John came into Calvin Klein for a VIP fitting (where her colleagues probably did go nuts). He then invited her to sit at his table at a gala, Carolyn's friend MJ Bettenhausen told Beller. But when Carolyn thought that another woman at the table was John's date, she got annoyed and declined his invitation to join him at an after-party.

Was Carolyn Seeing Someone Else When She Met John?

Carolyn did casually date Michael, a model who once worked as a hotel doorman, but not until the fall of 1992 and they were "much more off than on," per Beller's book.

And Bergin's claim in his 2004 book The Other Man that he continued having a sexual relationship with Carolyn, not just after she met John but until she died, was, Beller wrote, "considered questionable by many of Carolyn's friends."

Was JFK Jr. Super Late to His First Dinner Date With Carolyn?

In Love Story, Carolyn waits 20 minutes at an Indian restaurant for John and is leaving when he shows up on his bicycle.

Which he leaves unlocked, only to come out of their hours-long date to find it's been stolen. So, he gets to walk Carolyn home.

"I thought I had more time," he said as they arrive at her building's front door. She asks, "More time for what?" and they kiss. He asks if he'll see her again and she assures him, "I had a nice time tonight" before calling it an evening.

IRL, these two had a first date somewhere, and it's perfectly conceivable that John rode his bike and was late, but otherwise this two-kindred-spirits-bonding-over-beers tableau was created for the series.

Daryl Hannah Shows Up at John's Loft After His First Date With Carolyn

Daryl Hannah (Dree Hemingway), John's on-again-off-again girlfriend, is at his loft when he comes home after he was just rhapsodizing to his cousin and best friend Anthony Radziwill (Erich Bergen) about how all he wants to do is call Carolyn.

Soon, he's bringing Daryl to cousin Edward Kennedy Jr.'s wedding in October 1993, much to his mother Jacqueline Kennedy's disapproval (poured on here for effect, but based in reality), and Carolyn finds out from a tabloid cover that her seemingly eager suitor is back on with his movie star ex.

Meanwhile, John has been sending Carolyn flowers, eventually telling her when they bump into each other at another event that he "can't seem to function" knowing that she hated him. To which she replies, "I don't know you well enough to hate you."

The surprise rendezvous was a dramatic way for Love Story to introduce the Splash star, but producers didn't seek input from Daryl, who's been married to Neil Young since 2018.

"We want to find these characters from the inside out," producer Nina Jacobson told Gold Derby, "and it's hard to serve a bunch of agendas when you [go] to the real people. So we tend not to do that except in rare cases."

In Daryl's case, she's "an adversary to what you want narratively in the story," Jacobson explained, but "we still try to really show respect to the fact that she does have a fluency with this [celebrity] world that Carolyn doesn't have."

What Really Happened to Dary Hannah's Dog?

In the series, John coming home to find Daryl entertaining a bunch of her kooky friends is a sign that the end is nigh. She finally leaves him, challenging him to figure out what he really wants.

Daryl says she'll be back for her dog Hank. Instead, John is asked for an autograph while walking him, and he loses the leash and Hank is fatally hit by a cab. John then flies to L.A. to bring Daryl her beloved pet's ashes.

True story: John's friend Sasha Chermayeff said his pal was walking Hank in Central Park when the dog got off leash and was hit by a car in May 1994, per RoseMarie Terenzio and Liz McNeil 2024 book, JFK Jr.: An Intimate Oral Biography.

"So, he goes out there [to L.A.] to bury the dog," friend Steven Gillon said in the book. "And while he's out there, his mom has a dramatic turn for the worse. He was deeply resentful that Daryl dragged him out there to attend a funeral for her dog when his mother was dying of cancer."

In Love Story, mom Jackie (Naomi Watts) leaves a message for John, seemingly while he's on the plane, before collapsing in her apartment. That was conceived for effect, but it's meant to hammer home how sick the former first lady was after being diagnosed with non-Hodgkins lymphoma in December 1993. She died on May 19, 1994.

What Was the Actual Timeline of John and Carolyn's Relationship?

John and Carolyn didn't see each other after the gala that went wrong until May 18, 1992, at a fundraiser.

Then they hit it off and dated throughout the summer before they cooled off for almost two years, according to Beller's book. Only after Jackie's death did they get together for good.

"In reality, they were on again, off again, a little bit more than we had time to do in the show," executive producer Brad Simpson told USA Today. "But we needed to jump ahead, and we didn't feel like the audience wanted to see the stop and starts of their romance."

JFK Jr. Forgets His Keys

When he brings Carolyn home to his loft for the first time, John realizes he forgot his keys.

While that's a made-for-TV moment, John IRL could be careless and was prone to losing his keys and wallet—an attribute that later made Carolyn reluctant to fly with him alone when he got his pilot's license.

In addition to that bit of foreshadowing, when John invites Carolyn to a party at his sister Caroline Kennedy Schlossberg's house, he doesn't tell his date it's actually a sit-down dinner for Caroline's birthday.

When she tells Carolyn not to worry, that John does stuff like that all the time, Caroline (Grace Gummer) clarifies, "I just mean that he's forgetful, not that he's bringing women unannounced."

Carolyn Meets Caroline for the First Time on Her Birthday

John really did bring Carolyn to meet his sister on her 37th birthday on Nov. 27, 1994, though the gathering at Caroline's Park Avenue apartment is described as a party, rather than a dinner, in Carole Radziwill's memoir What Remains.

And the Real Housewives alum, who was there with Anthony and thrilled to see Carolyn, wrote that her friend walked "into this guarded room radiant and stubbornly original. Impulsively affectionate."

Caroline hugged John and told Carolyn, "So nice to meet you," Carole recalled. "Her friends smile politely and then shift their focus to John."

According to Beller's Once Upon a Time, those who thought Carolyn and Caroline disliked each other at first sight had the wrong idea. An acquaintance who saw them lunching said, "The two women seemed to really enjoy each other, and the conversation flowed, peppered with laughter here and there."

John Gets an Anonymous Note Claiming Carolyn Is Bad News

After a game of touch football in the park with his buddies, John finds a handwritten letter in his gym bag claiming that Carolyn, among other things, finagled a meeting with him through her boss Calvin Klein because she was trying to "land" him. When she comes over later, John's fuming. Appalled that he was willing to believe any of it, she walks out.

Seemingly days later, he shows up at her apartment and declares himself "an idiot." Their heart-to-heart leads to him telling her he loves her for the first time.

John really did get such a letter detailing Carolyn's alleged hard-partying ways and busy personal life, per Beller, but it was earlier in their relationship. According to her book, after they dated in the summer of 1992, John unceremoniously broke it off after getting the letter, after which Carolyn resisted his efforts to apologize for more than a year.