Brooke Shields Once Went On A Painfully Awkward Date With John F. Kennedy Jr.
Brooke Shields is opening up about her past experience with John F. Kennedy Jr. A documentary on Shields' career and personal journey, "Pretty Baby: Brooke Shields," was released on Hulu on April 3, and numerous subjects have been featured in the film — including Shields' previous marriage to tennis star Andre Agassi. During an April 2023 USA Today interview, Shields discussed how her relationship with Agassi served its purpose, although it didn't work in the long run.
"That was an important stage and relationship in my life, and I don't regret it," Shields said of her time being married to the ex-athlete. "It afforded me a lot of space from my mother and gave me this belief in my own talent. That was one of the main beautiful purposes of the marriage." In addition, Shields shares information about other former flames in the documentary such as her ex-boyfriend Dean Cain. As Insider reported, Shields said she "wanted to jump into the personal relationship and the love and the commitment" with Cain. In March 2023, Shields told People she and Cain got back together once more before their final breakup. When it came to Shields and JFK Jr., their romance didn't quite work out.
Brooke Shields and John F. Kennedy Jr.'s date had a 'less than chivalrous' conclusion
Brooke Shields and John F. Kennedy Jr.'s first date didn't go smoothly. While visiting "The Howard Stern Show" recently, Shields revealed that she'd been crushing on JFK Jr. from a young age. "I was so madly in love with him since the time I was, like, 3. My mom would say, 'That's the boy you're going to marry,'" Shields said. Shields and JFK Jr. later ended up going on a date during an Aspen, Colorado ski trip. The two stopped by a bar, then went back to JFK Jr.'s hotel. JFK Jr. kissed Shields, which the "Blue Lagoon" star called "the best kiss [she's] ever had in [her] life." From here, Shields opted not to sleep with JFK Jr. in order to protect herself emotionally.
"I was so afraid of being really hurt because if I slept with him I would've given him my entire universe, my heart, my everything," Shields said. Rather than offering to drive Shields home, JFK Jr. let her leave via cab, which Shields said was "a little less than chivalrous." Following this, Shields said JFK Jr. "didn't look at [her], and he didn't talk to [her]," adding that "he showed his true colors." In 1996, JFK Jr. got hitched to Carolyn Bessette Kennedy, per People. The couple, along with Bessette's sister, then tragically died in a 1999 plane crash, History wrote. Shields, meanwhile, found long-term love with a different partner.
Chris Henchy 'made such a strong impression' on Brooke Shields from day one
Years after her less-than-ideal date with John F. Kennedy Jr., Brooke Shields encountered her perfect partner. As Us Weekly wrote, Shields recalled meeting producer-slash-writer Chris Henchy in "Down Came the Rain: My Journey Through Postpartum Depression," a memoir she penned in 2005. "I left without even knowing his full name, but he made such a strong impression that I called up a friend and told her I had found a guy," Shields said of her first time running into Henchy. She and Henchy then started their connection as a friendship, and it eventually became romantic. "Finally ... I had to admit that there was something between us that I could no longer ignore, and we started dating," Shields said.
In a March 2023 interview with People, Shields detailed that she broke things off with Henchy before the two reconnected and wed in 2001. The pair went on to have two daughters together named Rowan and Grier. Shields has publicly displayed her love and admiration for Henchy. In a June 2021 Instagram post featuring throwback family photos in honor of Father's Day, Shields called her hubby "the best dad." Furthermore, while celebrating Thanksgiving in 2020, Shields shared a photo of herself, Henchy, and their two daughters, writing, "Thankful for them."