Brooke Shields is opening up about one of the most talked-about connections from her past. During an appearance on “Watch What Happens Live” Thursday night, the iconic model and beloved Hallmark actress addressed long-standing speculation about her relationship with the late John F. Kennedy Jr., revealing the truth behind their bond.
GettyShields admitted she had a major crush on the public figure but made it clear their relationship never became physical. The revelation offers a candid look at one of Hollywood’s most whispered-about romances from her younger years.
Brooke Shields Sets the Record Straight on Her Relationship with John F. Kennedy Jr.
“I had a crazy, crazy crush,” Shields shared. “We dated, but I never slept with him.”
“I don’t know if that counts. It counted for me!” she added. “He was lovely to meet.”
NBCUniversalThe conversation came as Shields reflected on watching FX’s Love Story, which explored Kennedy Jr.’s relationship with Carolyn Bessette Kennedy before the couple’s tragic 1999 plane crash.
Getty“I watched it start to finish. I loved it. I thought the acting was amazing,” Shields said, while clarifying that she and Kennedy Jr. never had “a real love story.”
Brooke Shields’ Daughter Discovered the Family Connection on Set
GettyWhat happened next turned into an unforgettable mother-daughter moment. Shields’ 23-year-old daughter, Rowan Henchy, was working as a production assistant on “Love Story” when she stumbled upon a surprising mention of her famous mom in the script.
The discovery led to an immediate phone call. “That was a little weird,” Shields told People. “I was away, and my daughter called me and she says, ‘Oh my God, you’re mentioned in “Love Story,”‘ and she’s like, ‘Is it true?'”
The scene in question features Kennedy Jr., portrayed by Paul Anthony Kelly, revealing to Carolyn, played by Sarah Pidgeon, that he and Shields had shared a kiss despite never officially dating.
When Rowan pressed her mother for answers, Shields didn’t hold back. “I was like, ‘OK, I’d be happy to tell you all the stories if you want,'” the actress recalled, “‘but yes.'”
Shields Previously Opened Up About Their ‘Best Kiss’ & Why She Held Back
This isn’t the first time Shields has shared memories of Kennedy Jr. During a 2023 appearance on “The Howard Stern Show,” the actress offered a deeper glimpse into their brief romance.
Shields revealed the two went on what she described as one “real” ski date in Aspen, Colorado. When it came to their chemistry, she didn’t mince words — calling their kiss the “best kiss [she’s] ever had in [her] life.”
GettyBut despite the undeniable connection, Shields found herself holding back. The idea of taking things further felt overwhelming.
“I was like, ‘Oh my God, you’re falling in love and if you sleep with him, he may not talk to you again,'” she recalled.
Shields made it clear her hesitation wasn’t about playing games — it came from a place of genuine fear. “I wasn’t playing a game, I really was just so afraid of being really hurt,” she explained. “Because if I slept with him, I would have given him my entire universe, my heart, my everything.”
Kennedy Jr. Married Carolyn Bessette & Shields Found Love With Chris Henchy
GettyKennedy Jr. went on to marry Carolyn Bessette in 1996, and their relationship captivated the public throughout the late 1990s.
Tragedy struck in July 1999 when Kennedy Jr., Carolyn, and Carolyn’s sister, Lauren Bessette, died after the small plane Kennedy Jr. was piloting crashed into the waters near Martha’s Vineyard, Massachusetts.
GettyShields also found her own path forward. The actress married tennis star Andre Agassi in 1997, though the couple divorced in 1999.
She later tied the knot with Chris Henchy in 2001. The couple now shares two daughters together — Rowan and Grier Henchy.
