Carolyn Bessette enjoyed a wild and free four 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 enrolled in Boston University in 1983, majoring in elementary education. However, outside of her studies, a former friend reportedly dubbed Bessette a “campus maneater.”
During her sophomore year at college, the late fashion icon — who was raised in Greenwich, Connecticut — dumped her football playing high school sweetheart, Eugene “Gene” Carlin, for “star college athlete” John Cullen. Bessette also dated fashion heir Alessandro Benetton.
Not only did the former Calvin Klein employee have a rich love life during her early twenties, but Bessette also tried to jump start her modeling career.
In newly unearthed modeling pictures, obtained by Daily Mail, Bessette can be seen posing in various stunning shots.
One snap captured her sitting on a bale of hay in a black, low-cut dress, barefoot with her legs spread open, while another shows her sitting up against a tree in a sweater and jeans. She rested with her chin in her hands as she smiled for the camera.
Bessette was serious about launching a life in front of the lens, even appearing on the cover of BU’s 1988 calendar.
Despite Bessette’s efforts, her modeling career didn’t take off, and instead, she began working for John Lyons, who ran Boston nightlife.
“Carolyn was very good at her job,” a former pal of Lyons told the New York Times in 1996. “She had a lot of hands to hold, and she did it very well.”
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“Being in the circles she was in, young men with power and influence were hitting on her frequently,” the friend revealed. “She’s had offers of courtship and marriage from every Saudi prince from here to the Middle East in those clubs.”
Once Bessette moved to the Big Apple — where she worked as a fashion publicist for Calvin Klein — her love life amped up.
She went on to date Will Regan, the NYC nightlife impresario and Calvin Klein model Michael Bergin.
“He was a breathtaking man. He was a real beauty,” a friend of the model told Page Six.
Bessette began dating Kennedy in 1992, with an insider admitting that the lawyer was a little jealous of Bergin.
“Do I think she used Michael to get John jealous? I think Michael got John jealous. Carolyn was too smart to not be aware of that … She loved Michael,” a source close to both Bergin and Bessette shared.
The insider believes that Bessette’s feelings for Bergin never totally faded even after she married Kennedy in 1996.
Bessette and Kennedy’s relationship was famously volatile, with rumors of infidelity and impending divorce before their lives were cut short in a 1999 plane crash.
And despite Bessette coming across as aloof — even on FX’s “Love Story,” Bergin (played by Noah Fearnley) tells Carolyn (Sarah Pidgeon) that she “is the most guarded and elusive woman I’ve ever met” — sources recall the blonde beauty being more calculated in real life.
“She was very aware of her appeal,” the source told Page Six.
“She was beautiful. She had the full package. When she was talking to you — everyone [else] disappeared. It was just her and you. She made you feel like you were the most interesting and attractive person she had ever met.”
