
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.”
And immediately, the suitors followed.
“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.”
News
Parents’ Heartbreaking Regret: They Found Their Autistic Daughter’s Secret Diary Too Late – The Dreams She Never Got to Live
Melissa Oelke, a 21-year-old creative and talented art student, was found deceased in Madison County, Illinois, just days after she…
Heart-Shattering Discovery in the Ashes: Husband Finds Wife’s Scorched Medical Records Hidden in Their Burned Home — The Secret She Never Told Him
In the quiet suburb of White Bear Lake, Minnesota, what was supposed to be an ordinary family home turned into…
“Wife Tried to Shove Me Off a Cliff First!” Hawaii Doctor Claims Self-Defense in Shocking Birthday Hike Attack – Directly Contradicting His Own Son’s Bombshell Testimony
Hawaii anesthesiologist Gerhardt Konig took the stand this week in his attempted murder trial one year after he allegedly tried…
Smiling in His Last Photo — But Eric’s Final Message to Friends Hid a Terrifying Secret That Shattered Everyone
The vibrant smile in Eric Fernando Gutierrez Molina’s last photo told one story — a joyful young man living his…
Heartbreaking Discovery: Flight Attendant’s Family Finds Medical Papers Just 2 Days Before His Tragic Death in Colombia
In a devastating revelation that has left friends, colleagues, and the aviation community in shock, the family of 32-year-old American…
Devil’s Breath Horror: American Airlines Flight Attendant Lured to Death After Wild Medellín Night Out – Body Found in Rural Colombia
A 32-year-old American Airlines flight attendant from Dallas, Texas, met a tragic end during what was supposed to be a…
End of content
No more pages to load




