Tour the homes of JFK Jr. and Carolyn Bessette's Love Story

A real-life Love Story

Recently romanticized into a hit Disney+ limited series by Ryan Murphey, the real-life Love Story between Carolyn Bessette and John F. Kennedy Jr. was as fascinating to their 90s contemporaries as the TV show was to modern-day fans.

JFK Jr., son of the late President Kennedy and widely decreed ‘sexiest man alive,’ reportedly fell head-over-heels for the stylish fashion publicist after a chance encounter in the Calvin Klein showroom, and the rest, as they say, is history. 

Click or scroll on to discover the many places this famous pair called home.

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Carolyn's upbringing

Carolyn Bessette was born in White Plains, New York, but grew up in Old Greenwich, Connecticut with her mother, stepfather, and two older sisters. Her childhood home, pictured here, was a typical clapboard-clad New England colonial.

Carolyn went on to attend Boston University where she studied elementary education. But instead of pursuing a career in teaching, she became a saleswoman at Calvin Klein in a local mall. It was there that she was scouted by a traveling sales coordinator impressed by her grace, style, and charm, and promoted to a more high-profile position in New York City.

A childhood in the spotlight

While Carolyn grew up far from the spotlight, John’s childhood could not have been more different. John was just three years old when his father, President Kennedy, was brutally assassinated, thrusting him and his family even further into public scrutiny.

After the assassination, the Kennedys moved briefly to a townhouse in Georgetown, D.C., where he is pictured here with his mother, Jackie. Shortly after, the young family moved to a luxurious apartment on the Upper East side of Manhattan.

Years at Brown

John went on to attend Brown University, where he spent his first year in Littlefield Hall, pictured here.

Having been plagued by press and photographers for most of his childhood, John received a brief reprieve from the paparazzi during his time at Brown, enabling him to focus on his degree in American studies, his extracurricular activities, including acting and founding a political discussion group, and his social life, joining the fraternity of Phi Psi.

Post-graduation adjustment

After college, John took a break, traveling to India to do postgraduate work at the University of Delhi. He ultimately returned to New York, working a series of jobs ranging from a role in the Office of Business Development to one in the 42nd Street Development Corporation to a summer associateship with a law firm.

He went on to earn a JD from NYU Law School, but failed the bar exam twice before finally passing it on his third attempt, a fact that was widely publicized by the press.

166 Second Ave in the East Village.

Carolyn’s first New York apartment was 166 Second Avenue in the East Village, a neighborhood which was, at the time, considered quite rough. “I used to step over drunks and crack dealers to get to my apartment,” she reportedly told WWD.

“Everybody at Calvin thought I was crazy, but I couldn’t imagine coming to New York and living anywhere else. Even with all the weirdness, I felt comfortable and I had fun,” she claimed.

A humble abode

According to her ex-boyfriend Michael Bergin, the apartment was quite tiny. “It was a nice building, a doorman building, but the apartment was unbelievably small – even by New York standards. As you entered, there was a microscopic kitchen to the right, a bathroom to the left, and the rest of the place – maybe ten or twelve square feet – was home.

There was a box spring and mattress pressed up against one wall, and a closet just beyond that didn’t even begin to hold her clothes,” he wrote.

Romance and career success

Carolyn had moved to New York to work with Calvin Klein’s high-profile clients, including actress Annette Bening and newscaster Diane Sawyer. She rose quickly through the ranks of the company, earning her stripes through her business savvy, and her efforts to make then-unknown model Kate Moss the face of the brand.

Her career blossomed in tandem with her romance with John, and she eventually left the East Village behind for Greenwich Village, and a Federal-style townhouse around the corner from Washington Square Park.

112 Waverly Place in Greenwich Village.

Remarkably, Kate Moss also lived in the elegant townhouse on Waverly Place, in a separate apartment at the back of the property. However, it was not the supermodel who soon had paparazzi camping outside the house’s front door.

Photographers quickly uncovered Carolyn’s new address and, eager for shots of JFK Jr.’s new flame, began staking out her apartment, forcing her to move yet again.

'Home Depot'

Bessette and Kennedy had begun dating in 1994. By the summer of 1995, Carolyn moved into John’s Tribecca apartment, which he had purchased for just $700,000 in 1994, according to realtor.com.

While there are no photos of the couple’s top-floor, two-bed apartment inside the North Moore Street complex, their love nest was reportedly very modest with an industrial aesthetic that inspired John’s nickname for it: 'Home Depot.'

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The Tribeca apartment

Another apartment within the building, last listed with Compass, gives a sense of the industrial, open-plan interior layout the Kennedy pad likely shared. Its high, beamed ceilings, supporting columns, and large windows were all synonymous with the typical Tribeca loft conversion of the 1990s.

A private wedding

To avoid the throngs of press and prying eyes, the wedding itself took place on the remote island of Cumberland in Georgia, in the tiny wooden chapel of the First African Baptist Church.

The candlelit ceremony was attended by close friends and family, who reportedly had to present a special Indian nickel upon arrival on the island to gain access, else they were escorted from the premises.

Hiding from the press

After their wedding, the couple returned to find the press yet again camping out on their doorstep. While John was all too familiar with media interest, Carolyn struggled to adjust to life in the spotlight.

Having left Calvin Klein as her relationship with John intensified, she found it hard to find another job without accusations that she was either exploiting her fame or causing too much distraction. Instead, she took to haunting their Tribeca apartment, only occasionally venturing out for public appearances with John.

Out on the town, or out of town?

While the couple never had the opportunity to move, they were reportedly contemplating an escape from the city before their untimely deaths, eyeing up a lavish home in New Canaan, Connecticut.

The Kennedy compound

The couple did have access to a country escape, though perhaps not one as private nor as restful as Carolyn might have wished. In true Kennedy fashion, John and Carolyn spent plenty of time out at the family compound in Hyannis Port, where John had been brought and indeed photographed so often as a little boy when Kennedy was still in office.

A coastal reprieve

John had begun taking Carolyn out to Hyannis Port early in the relationship, using the trips to introduce her to his family, and help her get used to the intense Kennedy family traditions and customs.

While these visits may have been something of a baptism by fire for Carolyn, they did at least provide some reprieve from the constant bombardment by paparazzi the couple faced in New York.

The plane crash

Tragically, it was not far from the Hyannis Port sanctuary that John, Carolyn, and Carolyn’s older sister Lauren died in a plane crash on July 16, 1999, just off the coast of Martha’s Vineyard. John, who was in the process of getting his pilot’s license, lost control of the plane while transporting his wife and sister-in-law to a wedding on the Vineyard.

The outpouring of grief in response to the news was nearly on a par with that of Kennedy’s assassination. Pictured here, mourners piled flowers and tributes outside the door to the couple’s Tribeca apartment.

An immortal love story

While their lives were cut short by tragedy, Carolyn Bessette and John F. Kennedy Jr.’s lives had enormous impact on cultural memory and popular media.

They were remembered for their effortless elegance, youth, vivacity, and enduring love in the face of adversity, and have inspired numerous memoirs by people who knew them, and fictionalized films and TV series by those who wish they had.

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