John F. Kennedy Jr. and Carolyn Bessette are generally reported to have first met in the early 1990s, most often cited as 1992, when she was working for Calvin Klein in New York and helped him as a VIP client in the store.

Quick Scoop: Their First Meeting

Most reputable biographies and features describe their first encounter taking place at Calvin Klein’s New York City location, where Carolyn was a sales associate handling VIP customers. John, then in his early 30s, came in to select suits, and Carolyn was assigned to help him, which is widely described as the spark of their connection.

Some accounts place this first meeting “around 1991,” but major recent retrospectives and timelines attached to the new TV dramatizations of their story now usually settle on 1992 as the year they met. Either way, it was the early 1990s, in that Calvin Klein setting, before they became the intensely followed couple that dominated late‑90s tabloid culture.

A Bit of Storytelling Context

From that first meeting, multiple sources say John was immediately intrigued by Carolyn’s cool, self‑possessed demeanor and the fact that she did not seem overly impressed by his fame. Accounts from friends and journalists note that he pursued her for some time while both were still dating other people, including his on‑and‑off relationship with actor Daryl Hannah.

By the mid‑1990s, the relationship had turned serious, leading to his 1995 proposal and their secret 1996 wedding on Cumberland Island, which only deepened the public fascination with how an encounter in a designer showroom evolved into one of the most mythologized relationships of the decade.

Mini FAQ

  • Where did they meet?
    At a Calvin Klein store in New York City, where she was working with VIP clients.
  • When did they meet?
    Early 1990s, most commonly reported as 1992.
  • What was he doing then?
    John was a lawyer and high‑profile public figure, soon to launch George magazine; she was rising within Calvin Klein’s fashion world.
  • Why is this a trending topic again now?
    Their relationship is back in the spotlight because of recent and upcoming dramatizations and documentaries, including an FX series revisiting their “love story” and its tragic end.

Is there anything specific you’d like next—more about how their relationship developed after that first meeting, or more about the recent TV portrayals and “latest news” around them?