A Quarter of a Century of Love and Growth
Brooke Shields is celebrating an important milestone in her life: her silver wedding anniversary with her husband, Chris Henchy. On Tuesday, the 60-year-old actress shared a heartfelt message on Instagram, writing, “Today marks 25 years married!” She added, “A quarter of a century… does this make us an old married couple?? I love you, Henchy!!” The post was accompanied by several photos from their wedding day, captured by photographer Lara Porzak.
Their relationship began quickly. They met in 1999, became engaged in 2000, and tied the knot in 2001. Soon after, they welcomed two daughters: Rowan, now 23, and Grier, 20. Shields has often spoken about the secret to their long-lasting marriage, emphasizing the importance of communication. “I think you have to constantly make sure you discuss things rather than let them fester,” she told People two years ago. “And you have to be willing to adapt.”
Shields’ journey to her current relationship wasn’t without its twists. Before meeting Henchy, she had been in several high-profile relationships, including marriages to Dean Cain, John Travolta, and Andre Agassi, whom she was married to from 1997 until 1999. She also admitted to a brief fling with the late John F. Kennedy Jr. in the 1980s.


Henchy, who is 62, is a director, film producer, and screenwriter. He is best known for his collaborations with Will Ferrell, working on films such as Land of the Lost, The Other Guys, and The Campaign.
In May 2024, Shields spoke to People about how she keeps the spark alive in her marriage. “Sometimes you don’t grow and change at the same rate,” she said. “And that can be really hard because what you initially fell in love with looks different. It doesn’t mean it’s bad, it just is different.” She added, “It’s like we have to get to know each other as people at this age, whereas we met in our early 30s.”
She emphasized the need for couples to adapt over time. “The things that were cute in the beginning aren’t cute now,” she said. “So I’ll be like, ‘That doesn’t fit with me anymore. Can we find another way of ribbing me? That doesn’t feel good anymore. It felt good in my 30s. It doesn’t feel good in my late 50s.’”

Shields recently opened up about her brief relationship with John F. Kennedy Jr. nearly 40 years ago. The pair met on a skiing trip in Aspen, Colorado, when she was in her early twenties. During an appearance on Watch What Happens Live With Andy Cohen, she confirmed they dated but the relationship never became physical. “I didn’t have a love story, I had a crazy, crazy crush,” she said. When asked if they ever had sex, she replied, “We dated but I never slept with him, so I don’t know if that counts… He was lovely to me.”



Kennedy’s relationship with his wife, Carolyn Bessette Kennedy, was explored in Ryan Murphy’s TV show Love Story. Shields admitted she binged the entire series. “I watched it start to finish. I thought the acting was amazing,” she said. She also revealed that her daughter Rowan worked as a production assistant on the show and had informed her that her name would be mentioned in the series.
“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?’” Shields recalled. “I was like: ‘OK, I’d be happy to tell you all the stories if you want, but yes [it’s true].’”


Shields also shared a memorable moment from her time with Kennedy. During an appearance on The Howard Stern Show in 2023, she described a kiss they shared. “He kissed me, and it was like the best kiss I’ve ever had in my life. It was beyond not disappointing. The lips are beautiful, and the face is amazing, and the body and the person, and he was down to earth and funny and irreverent.”
She added, “It was beyond not-disappointing. I froze, though, because he was so precious to me. I was like: ‘Oh, my God, you’re falling in love, and if you sleep with him, he may not talk to you again – and you can’t handle that.’ I wasn’t playing a game. I really was just so afraid of being really hurt, because if I slept with him, I would’ve given him my entire universe, my heart, my everything.”
Kennedy and his wife, Carolyn, were killed in a plane crash in 1999, which also claimed the life of Carolyn’s sister, Lauren.






