John F. Kennedy Jr.’s Lovers Tell All! What It Was Like Dating the Late ‘Adventurous and Romantic’ Hunk

During the 1980s and early ’90s, John F. Kennedy Jr. was America’s most eligible bachelor. Blessed with smoldering good looks, the athletic 6-foot-1 Kennedy heir (son of slain U.S. President John F. Kennedy and his socialite wife, Jacqueline Kennedy Onassis) had his pick of the litter before he eventually settled down with fashion publicist Carolyn Bessette in 1996.

The Brown University grad — who tragically died at the age of 38 alongside his wife and her sister when their small plane crashed while en route to a family wedding in Martha’s Vineyard, Massachusetts, in July 1999 — certainly took advantage of his charmed position, romancing the likes of Sarah Jessica Parker, Daryl Hannah, Brooke Shields, Sharon Stone and Madonna. Now Closer can reveal, using his famous exes’ own words, what it was really like to date, love — and bed! — the charismatic political scion.

JFK Jr.’s Lovers Kissing and Telling!

The lawyer turned magazine publisher knew how to sweep women off their feet. Sex and the City actress Sarah Jessica Parker — who rebounded from her relationship with Robert Downey Jr. with John in 1991 — was elated when he wanted a date. (SJP’s showbiz pal, director Adam Shankman, told a magazine she’d called him screaming, “You’re not going to believe who asked me out!” after Kennedy first made his move.)

A source previously told Closer that John “treated her well and made her feel special.” She returned the favor: One memorable night, she popped out of a limo to meet him in a coat — and nothing else!

John’s girlfriend of four years Christina Haag has said the self-confessed adrenaline junkie was an “adventurous and romantic” lover. (They were together between 1985 and 1989.) In her memoir, Come to the Edge, she wrote that John was full of surprises. “One time he left red roses tied to my bicycle — two dozen red roses and an unsigned card that said, ‘You rule my world,’” she revealed. She called kissing him “magical” and said he was curious about tantric sex and had brought a book about it on vacation.

During a 2023 interview with Howard Stern, Brooke Shields told the shock jock that she shared “the best kiss I’ve ever had in my life” with JFK Jr. in the 1980s. “It was beyond not-disappointing,” she said. “The lips are beautiful, and the face is amazing, and the body.”

And Sharon Stone reportedly had a steamy two-night fling with John in Martha’s Vineyard in 1995. “It only lasted a few days,” an insider told Closer, “but Sharon still considers it one of the most romantic encounters she’s ever had.” There was one person John reportedly couldn’t please: Madonna. He and the uninhibited Material Girl hooked up in 1988 but “he was far too straight for her sexually,” a friend of the singer said.

John F. Kennedy Jr.’s Mom Jackie Kennedy Onassis Meddled in His Love Life

Prior to her 1994 death, John’s mom, Jackie, had a vested interest in her son’s love life, and she often meddled. (She’s the one who’d set him up with Brooke.) “It had always been tough for his girlfriends to meet Jackie for the first time,” J. Randy Taraborrelli wrote in The Kennedy Heirs. Stunning Splash star Daryl Hannah didn’t pass Jackie’s test. “Daryl was an actress, and people in Jackie’s high-society world didn’t want to associate themselves with those types of people,” a source told Closer.

John and Daryl ultimately ended their on/off relationship in 1994 in part because she couldn’t handle the media attention and felt humiliated by John’s hesitance to propose. “I get asked about [marriage] all the time,” she once said. “Even [my plumber] asks me. I’m just trying to get my pipes fixed. Why can’t people talk about something else?”

John F. Kennedy Jr. Was a Nice Guy

By most accounts, John was a ladies’ man, but not a heartbreaker, and he remained on good terms with most of his ex-girlfriends years after they broke up. Says his model ex Julie Baker: “John was a normal, humble, great guy.”