Carolyn Bessette spent four wild and free years at Boston University in the mid-’80s before moving to New York City and falling in love with John F. Kennedy Jr.
The publicist attended Boston University in 1983 and majored in elementary education. But outside of school, a former friend described Bessette as a “campus man-eater.”
The late fashion icon, who grew up in Greenwich, Conn., dumped her high school football sweetheart, Eugene “Gene” Carlin, for “college star” John Cullen during her sophomore year. Bessette also dated fashion heir Alessandro Benetton.
Bessette, a former Calvin Klein employee, not only had a thriving love life in her early 20s, but also tried to launch a career as a model.
In newly unearthed modeling photos obtained by the Daily Mail, Bessette is seen posing in a variety of stunning shots.
One photo shows her sitting barefoot on a hay bale with her legs apart, wearing a low-cut black dress, while another photo shows her sitting leaning against a tree wearing a sweater and jeans. She rested her chin in her hands as she smiled for the camera.
Bessette was serious about starting her life in front of the lens, even appearing on the cover of BU’s 1988 calendar.
Despite Bessette’s efforts, her modeling career never took off, and she instead began working for Boston nightlife owner John Lyons.
“Carolyn was very good at her job,” a former friend of Lyons told The New York Times in 1996. “She held a lot of hands and did a very good job.”
And suitors soon followed.
“In her circles, powerful and influential young people often attacked her,” a friend revealed. “She’s had courtships and marriage offers from all the Saudi princes in these clubs, from here to the Middle East.”
Her love life further accelerated when Bessette moved to the Big Apple, where she worked as a fashion publicist for Calvin Klein.
She then went on to date Will Regan, a New York nightlife impresario and Calvin Klein model Michael Bergin.
“He was a breathtaking man. He was absolutely beautiful,” a friend of the model told Page Six.
Bessette began dating Kennedy in 1992, and sources admitted the lawyer was a bit jealous of Bergin.
“Do you think she used Michael to make John jealous? I think Michael made John jealous. Carolyn was too smart to realize that…she loved Michael,” said a source close to both Bergin and Bessette.
Sources believe Bessette’s feelings for Bergin never fully waned even after she married Kennedy in 1996.
Bessette’s relationship with Kennedy was famously rocky, with rumors of infidelity and impending divorce, before her life was cut short in a 1999 plane crash.
And while Bergin (played by Noah Fearnley) tells Carolyn (Sarah Pidgeon) on FX’s Love Story that Bessette seems aloof, saying she is “the most cautious, elusive woman I’ve ever met,” sources say the blonde beauty was more calculating in real life.
“She was very aware of her attractiveness,” a source told Page Six.
“She was beautiful. She had it all. When she was talking to you, everyone else disappeared. It was just her and you. She made you feel like she was the most interesting and charming person you had ever met.”
