The "Sexiest Man Alive" had a strategy.
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JFK Jr Dating
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John F. Kennedy Jr. may have lived the bulk of his adult life as the world’s most eligible bachelor, but he really didn’t want people to think he was single — in fact (for obvious reasons), he rarely was.

In America’s Reluctant Prince: The Life of John F. Kennedy Jr., historian and friend of Kennedy’s, Steven M. Gillon, writes, “John was neither as monogamous as some friends claimed nor as promiscuous as the tabloids suggested.” The media painted John as a playboy, but that was actually a strategic move on his part — if he was ever perceived as being single, he’d be inundated with “dating offers.”

“'John described receiving messages from distant contacts in his father’s administration and members of far-flung aristocratic families proposing introductions, which he gracefully sidestepped,'” John’s friend Barbara Vaughn told Gillon. “John would be monogamous for long periods of time, but once he felt the relationship fizzling out he would search for a replacement before breaking up,” Gillon explained.

Naturally, this led to a bit of overlap … Gillon recounts an instance in which John was in bed with a woman when the phone started ringing. After if stopped he took it off the hook to prevent further interruptions. Unfortunately, he’d picked up a little too early and left his current girlfriend on the line, listening while he had sex with another woman. Both women soon realized what happened, and perhaps testament to John’s charm, both eventually forgave him.

The former “Sexiest Man Alive” eventually found his match in Calvin Klein publicist Carolyn Bessette. Though John’s cousin’s widow Carole Radziwill claims that at one point he dumped Bessette to get back together with ex-girlfriend Daryl Hannah, they eventually reunited and wed in a small and surprisingly private ceremony on Georgia’s Cumberland Island in 1996.

Municipal Art Society presents Jackie Onassis Medal to Stephen Swid
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While John and Carolyn’s relationship no doubt had its complications, Kennedy is thought to have remained faithful to his wife throughout their marriage. Gillon writes that John had told friends, “I wish I could cheat on her,” but couldn’t bear to “humiliate Carolyn the way his father had done his mother.” However, it seems the same could not be said for Bessette, who appears to have had an affair with Calvin Klein underwear model Michael Bergin.

Sadly, both tragically died in a plane crash on July 16, 1999.