The Full Timeline of Daryl Hannah and John F. Kennedy Jr.’s Relationship

She’s a widely known actor, at least among millennials and boomers, and she once had a lengthy relationship with one of the most high-profile presidents’ sons in U.S. history — John F. Kennedy Jr. We’re talking about Daryl Hannah, best known for her roles in classic films like Splash, Steel Magnolias, and Grumpy Old Men.

In case you didn’t know (and many people don’t), she and JFK Jr. were a thing back in the day. Apparently, her time with him was depicted in a not-so-flattering way in Ryan Murphy’s 2026 anthology series Love Story: John F. Kennedy Jr. & Carolyn Bessette. That has raised questions about when the two actually dated and whether any of the events portrayed in the show accurately represent their relationship. Here’s everything to know.

Before Carolyn Bessette-Kennedy came into the picture, there was Daryl Hannah. The actor first met JFK Jr. in the early 1980s, per People, while vacationing with their families on St. Martin, but that wasn’t when the romantic connection formed. That came shortly after 1988, when they reconnected at JFK Jr.’s aunt Lee Radziwill’s wedding.

She had married Herb Ross, a director who worked on Steel Magnolias, perhaps one of the most widely known films Daryl is famous for. Sometime after that, the two began dating, and by the early ’90s, they were being featured in tabloids, the outlet notes.

Daryl and JFK Jr. appeared to be quite the serious couple, with many assuming a wedding would come in the near future.

However, as described by Vanity Fair, their relationship was “highly volatile” and “tumultuous,” on-again, off-again, until it officially ended in 1994.

What’s interesting, though, is that during the time they were dating, JFK Jr. reportedly met and even dated Carolyn Bessette in the early ’90s. She was working for Calvin Klein at the time, and they met during a fitting in 1991 or 1992.

“He had gone to pick out some suits, and she helped him — she was the handler for a lot of the VIPs. He asked for her number, and they went out on a few dates,” RoseMarie Terenzio recounted in her biography with Liz McNeil, JFK Jr.: An Intimate Oral Biography, per Town & Country.

A friend of Terenzio’s recalled that there was definitely some overlap between JFK Jr.’s time with Carolyn and Daryl, but they believed “he was obsessed with Carolyn from the minute he met her.” But after Carolyn learned Daryl was in the picture, she and JFK Jr. drifted apart, until his mother, Jackie Kennedy, died in May 1994. That’s around the time he reportedly broke things off with Daryl and reconnected with Carolyn, and the pair went on to marry in 1996.

Despite their strong connection, they too had their ups and downs, though it’s unclear where those struggles would have led them. Because in 1999, the couple, along with Carolyn’s sister Lauren, died in a plane crash. They had taken off from Essex County Airport in the evening of July 16, 1999, to attend a wedding, but the plane, which was piloted by JFK Jr., went down in the ocean.

While Daryl and JFK Jr.’s relationship may have been rocky, based on commentary and publications, she released an op-ed in The New York Times on March 6, 2026, claiming that Love Story didn’t portray her or her relationship with JFK Jr. accurately.

“The choice to portray her as irritating, self-absorbed, whiny, and inappropriate was no accident,” Daryl explained of her character in the series.

She also stated that “the actions and behaviors attributed to [her] are untrue,” clarifying that she had “never used cocaine” or hosted parties with drugs, nor did she “pressure anyone into marriage.” She added, “I have never planted any story in the press. I never compared Jacqueline Onassis’s death to a dog’s.”

Based on Daryl’s op-ed, it would seem that the portrayal of her in Love Story shouldn’t be taken at face value.