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At the height of their fame, John F. Kennedy Jr. andCarolyn Bessette were the closest thing the U.S. has had to royalty. After JFK’s only son began dating the Calvin Klein marketing executive in 1994, the world was fascinated by their relationship. Bessette, in many ways, was considered the next Jackie Kennedy while JFK Jr., of course, was destined to become the next JFK.

A year after they began dating, in 1995, Kennedy dropped down to one knee and proposed to Bessette. A year later, in April 1996, the two tied the knot in a beautiful and ultra-secretive ceremony. Five years after they began their relationship, however, their romance came to an end as they tragically died in a plane crash off the coast of Martha’s Vineyard.

And though their romance may seem like a modern fairy-tale which was sadly cut too short at a glance, the two faced many struggles over the years, from infidelity rumors to intrusive paparazzi. Find out more about their passionate yet complicated relationship below.