John F. Kennedy Jr. dated several women before he got together with Carolyn Bessette, with a few especially well‑documented long‑term relationships.

Short answer

Before Carolyn, JFK Jr.’s most notable and serious relationships were with:

  • Jenny Christian (high school/Andover girlfriend)
  • Sally Munro (college girlfriend at Brown, around six years)
  • Christina Haag (early–mid 1980s, considered a major long-term love)
  • Daryl Hannah (on‑and‑off from the late 1980s until about 1994)

He was also linked to Madonna and other women more briefly.

Mini timeline: before Carolyn

  • Late 1970s: Dates Jenny Christian while at Phillips Academy Andover.
  • 1979–1985: Long relationship with Sally Munro while at Brown University.
  • Mid‑1980s–1990: Serious romance with actress and writer Christina Haag; she later wrote the memoir “Come to the Edge” about their relationship.
  • Late 1980s–1994: High‑profile, on‑and‑off relationship with actress Daryl Hannah, often described as his main partner directly before Carolyn.
  • Late 1980s: Reported brief fling with Madonna during his time with Haag.

According to multiple retrospectives, when he first met Carolyn in the early 1990s, he was still involved with Daryl Hannah, and there was some overlap before he fully moved on and began dating Carolyn seriously after his 1994 split from Hannah.

Forum and “latest news” angle

Recent entertainment pieces and forum discussions revisit his dating history because of new documentaries, books, and dramatizations about JFK Jr. and Carolyn, so his earlier girlfriends—especially Christina Haag and Daryl Hannah—are back in the spotlight. Commenters often frame Haag as his early “true love,” Hannah as the last serious partner before Carolyn, and Carolyn as the relationship where he seemed most determined to settle down.

“Who did JFK Jr. date before Carolyn?”
Most fans now answer: a long string of girlfriends, but Christina Haag and Daryl Hannah are the big ones people point to right before the Carolyn era.

Bottom note: Information gathered from public forums or data available on the internet and portrayed here.