Not Andre Agassi, Not Chris Henchy: This Star Gave Brooke Shields Her 'Best Kiss' Ever

Hollywood icon Brooke Shields has made a name for herself since the '60s thanks to films like "Pretty Baby" and "The Blue Lagoon," and as her fame has risen, Shields has shared her fair share of different types of kisses both on and off the screen. So, who gave Shields her top smooch? The answer is surprisingly not her current husband, Chris Henchy, the screenwriter and director who has been married to Shields for the last 25 years. It's also not her former husband, tennis star Andre Agassi, who she was married to from 1997 to 1999. 

As it turns out, a top-tier kiss was shared between Brooke Shields and John F. Kennedy Jr., son of former president John F. Kennedy. Shields went into the details of the kiss during a 2023 interview on "The Howard Stern Show," explaining that it was "the best kiss I've ever had in my life." She added, "It was beyond not-disappointing. The lips are beautiful, and the face is amazing ... and he was down to earth and funny and irreverent."

Even before Brooke Shields became the "face of an entire decade" in the '80s, as she described it to TIME in 2023, she'd been mesmerized by JFK Jr. from a young age. Through the years, the renowned model and global actor had grown from Vogue's youngest cover model to a celebrated female star, but like all of us, she still had her first giggly crush. But unlike the rest of us, Shields' crush gave her an ultra-memorable kiss. Oh, and she grew to love him. 

The first boy Brooke Shields ever loved was also John F. Kennedy Jr. In her "Howard Stern Show" interview, Shields gushed, "I was so madly in love with him since the time I was like three. My mom would say, 'That's the boy you're going to marry.'" While it may not have ended in marriage for JFK Jr. and Shields, the two did link up. In the '80s, they met at a ski resort in Aspen, Colorado, and soon after, they went on a date where the life-changing kiss occurred.

Even though things for the pair seemed to have halted after the kiss, it certainly made quite the impression on Shields. In a 2026 interview on the Andy Cohen-led "Watch What Happens Live," Shields said, "We dated, but I never slept with him. I don't know if that counts." She added, "It counted for me!"  

In addition to her two marriages and an epic kiss with JFK Jr., Shields' dating history has included some major stars in the sports and entertainment industries, like the later superstar Michael Jackson and "Taken" actor Liam Neeson. JFK Jr. also went on to find love with his wife Carolyn Bessette-Kennedy, who became a cultural icon for her simple yet chic beauty looks. The pair married in 1996 and remained together until their untimely passing in a fatal plane crash in 1999.