Inside Calvin Klein's Unconventional Love Story With Model Kevin Baker

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's 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.

Carolyn Says She Needs to Think About It When John Proposes

John proposes to Carolyn in a row boat after a trip to Hyannis Port, where she has just met his extended family—including his aunt, "undisputed matriarch" Ethel Kennedy (Jessica Harper)—for the first time.

But Carolyn says she needs to think about it, that there's "a lot of big stuff" they have to discuss first.

Per Beller, John first took Carolyn to the family compound (where he did sign up for a breakfast shift without her) for Labor Day weekend in 1994.

According to Terenzio, John popped the question on a boat during a jaunt to Martha's Vineyard over Fourth of July weekend in 1995, telling Carolyn, "Fishing is so much better with a partner."

And he did offer up a diamond and sapphire eternity band, but while in the show JFK Jr. says it used to belong to his mother, in real life John commissioned Jackie's longtime partner Maurice Tempelsman to design a ring that looked like his late mom's emerald and sapphire "swimming ring." (IRL he gave Carolyn both rings, per Terenzio.)

A close friend of JFK Jr. told People in 2017 that Carolyn made John wait about three weeks for an answer. Gillon wrote in his 2019 book American Prince that Carolyn didn't say yes but wore the ring and told friends they planned to marry. But Terenzio recounted in her oral history that Carolyn called afterward and told her they got engaged during the holiday weekend.

In either case, the couple were engaged for months before their infamous 1996 fight in Washington Square Park.

Calvin Klein's Marriage to Kelly Klein Is in Decline

Carolyn had the ear of her boss Calvin Klein, but she was also close friends with his second wife, photographer Kelly Klein.

In Love Story, Kelly (Leila George) pushes back when Calvin says—in the wake of a (real) New York Post cover blaring, "JFK JR. POPS THE QUESTION"—that Carolyn can't work for him anymore "if her personal life is going to become a distraction."

Kelly fires back, "All due respect, you're the last person to be lecturing anyone on discretion," to which Calvin says, "From the beginning you knew what you were signing up for."

The designer then asks Kelly to accompany her to a gala that night, "one last time," indicating they're splitting up.

IRL, Calvin and Kelly announced their separation in August 1996, saying in a statement at the time, per columnist Liz Smith, “We are still the best of friends. We have made a decision to live apart. We are respectful of one another. We hope to work out any issues between ourselves.” They finalized their divorce in 2006.

Now 83, Calvin has been in a relationship with model Kevin Baker, who's 46 years his junior, for 10 years.

Carolyn Does Not Attend the 1995 Launch of George

In Love Story, Carolyn doesn't attend John's press conference announcing the launch of George magazine, at which he unveils the publication's first cover featuring Cindy Crawford dressed as sexy George Washington.

She watches on TV from home, having reluctantly agreed that John didn't have a choice other than to issue a denial that he proposed, lest the rumors that she had left him hanging overshadow the George news.

Carolyn really did steer clear of the Sept. 7, 1995, launch. Terenzio—tasked with issuing a statement denying John was engaged, after a pic of Carolyn's ring sparked speculation—wrote that John and his partner Michael Berman thought her presence would be "too distracting" and "she wasn't that upset about that."

But John's longtime friend Sasha Chermayeff noted in the oral history that she thought at the time "the public denial of the engagement bothered [Carolyn] so much...That was the first sign of Okay, this is what life with him is going to be about."

The Truth About JFK Jr. and Carolyn's Fight in the Park

Episode five ends with Carolyn tearfully accepting John's proposal after they have an explosive argument while they're out with their dog.

Thanks to copious coverage of the couple's Feb. 25, 1996, blow-up, many aspects of the Love Story fight—John seeming to wrest Carolyn's engagement ring off her finger, John in tears as he sits on a curb, John yelling at Carolyn as she grabs the dog's leash, "You've got my ring, you're not getting my dog!"—are ripped right from the headlines.

But the series features them fighting over John's proposal denial—"None of this would have happened," he shouts, "if you'd accepted my proposal in the first place like a normal f--king person!"—when in reality they'd been engaged for about five months. (In the show, Carolyn tries on the ring and agrees to wear it when they're alone, but has not yet said yes to marrying him before the fight.)

In her oral history, Terenzio recalled that the couple fought over John "being taken advantage of by his friends."

They had gone to a wedding where they were seated next to a New York Times reporter covering the event for the "Vows" column, and "Carolyn thought it was a bulls--t thing to do to your friend," Terenzio wrote. She noted that Carolyn felt bad about the fight afterward, "but she was also angry at John because she felt she was trying to protect him, not wanting him to be taken advantage of."

Ethel Kennedy Summons Carolyn Bessette for a Chat

After Carolyn and John's fight in the park makes headlines, Ethel invites her nephew's fiancée to her Hickory Hill estate in Virginia.

Robert F. Kennedy's widow compassionately levels with Carolyn, telling her, "You'll never be given the benefit of the doubt again, as ugly and unfair as that is…These men, they will break your heart, they'll drive you crazy, they'll make you want to scream. Don't."

Ethel really did have Carolyn flown out to the house where, per J. Randy Taraborelli's 2019 book The Kennedy Heirs, she advised Carolyn that she'd simply have to rise above, period.

A friend who accompanied Carolyn told the author that Ethel said being a Kennedy wasn't easy. But, the mother of 11 continued, "Then I finally got it that the only way to survive in this family is to look in the mirror in the morning every single day and say, 'You know what? I am enough.' Plain and simple. That's it. 'I am enough.' Eventually it sinks in that, yes, you are enough, and that no one can ever take that away from you. Not even the Kennedys."

Carolyn also could never lose her temper like that again in public, Ethel said, per the book. "These men are hotheads," she warned. "Don't let them goad you into acting improperly in front of the whole world."

Why Carolyn Asked Caroline Kennedy to Be Her Maid of Honor

In the show, Carolyn tells her sister Lauren Bessette (Sydney Lemmon) that she's thinking of asking Caroline to be her maid of honor, explaining that her future sister-in-law seemed "so hurt" by not being involved at all in the wedding planning.

"I think she feels really excluded," Carolyn explains. "I just think it would go a really long way with her…I can't go into my wedding, my marriage, with her resenting me."

Lauren says, "This will mean nothing to her. And it would have meant everything to me."

Per Taraborelli, Carolyn asked Caroline to be maid of honor at John's request after his sister not only blamed Carolyn for the spectacle in the park, but also saw it as a sign they shouldn't get married. He felt "the only way to smooth things over" was to have Carolyn extend that invitation.

Did Calvin Klein Expect to Design Carolyn Bessette's Wedding Dress?

When Carolyn goes to Calvin to resign two weeks after the park fight, telling him she feared her personal life had become too much of a distraction, he admits he feels "a bit blindsided."

But, calling her "a bright light," he also tells her she'll "be in good hands" with Narciso Rodriguez—who previously worked for him—designing her wedding dress. After she leaves, he puts away his look book and we get a glimpse of a dress sketch in a drawer.

"Calvin was very upset" when Carolyn quit, a colleague told Beller. "He felt left behind."

But while in Love Story Calvin is tipped off about the dress because Carolyn had been photographed with Narciso (Tonatiuh) and Caroline, IRL Carolyn left her job before leaning into wedding planning.

Carolyn Bessette's Mom Shares Concerns About JFK Jr. Marriage in Rehearsal Dinner Speech

Ann Freeman (Constance Zimmer) is worried Carolyn is going to lose herself in this marriage. She tells her daughter that in private—and shares her concerns with everyone else during her toast at the rehearsal dinner.

"John's love is just so big," Ann says, "and I worried. How could Carolyn, how could anyone, manage to maintain their center of gravity around something that massive, that shiny?" She concludes saying she prays that Carolyn will be able to count on John to be where he's needed.

In a private moment, John tries to assure his future mother-in-law that her daughter is the center of his world.

While what exactly she said that night is unknown, John's friend Robert Littell wrote in his memoir The Men We Became that Ann "expressed reservations over the union, implying that it might not be in the best interest of her daughter."

And John, he wrote, was "visibly stung by his mother-in-law's remarks."

Littell also noted that, while he and some other guests headed to the beach to keep the party going, Carolyn, "wise woman, had gone to sleep hours ago." Meaning, Love Story's version of events—John and Carolyn falling asleep on the sand in each other's arms and going skinny-dipping the morning of their wedding—was dreamed up for romantic effect.

Carolyn Bessette's Wedding Dress Drama

Carolyn really did have a last-minute dress crisis when she realized Narciso's zipper-less creation would have to go over her head after her makeup had already been done.

Gogo Ferguson, who designed the couple's rattlesnake rib wedding bands, recalled in An Intimate Oral History that it was "like pouring cream over her body," and Narciso "was trying to sew her into the dress." Terenzio wrote that Narciso had to open and then re-close the neckline, after which they put a scarf over Carolyn's head to not muss her hair and makeup.

 The bride's friend Gordon Henderson, who designed John's wedding tux as well as the groomsmen's suits, told Town & Country he provided a face-saving handkerchief, recalling, "When a friend is getting married, you do all that you can to make sure the couple feels satisfied and happy."

Alternately, Beller's Once Upon a Time has Carolyn having to redo her hair and makeup after putting the dress on.

Either way, the ceremony started at 7 p.m. rather than 5—John was also late, having misplaced his shirt—which necessitated the use of candles because the 19th-century wood-frame First African Baptist Church had no electric lights.