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Fox News
5 Apr 2023


Brooke Shields has had an extraordinary kiss in her life, and it was not with her husband, Chris Henchy.

During an appearance on "The Howard Stern Show," Shields, 57, revealed that the best kiss of her life was with John F. Kennedy Jr.

Since the actress "was like 3," she was "so madly in love" with John F. Kennedy's son. "My mom would say, 'That's the boy you're going to marry,'" she quipped to Stern.

Several years later, Shields met her heartthrob while on a ski trip in Aspen, Colorado.

BROOKE SHIELDS REMEMBERS BEING 'MOST FAMOUS VIRGIN IN THE WORLD'

Brooke Shields said John F. Kennedy Jr. was "the best kiss of my life."

Brooke Shields said John F. Kennedy Jr. was "the best kiss of my life." (Getty Images)

"He kept saying I looked like his mother, which was really interesting and a compliment, [but] I also was like, 'I don't know how to feel about this,'" she recalled of the moment. "Then we did have a real date. And I wouldn't sleep with him because I kind of loved him too much."

The "Blue Lagoon" star said the date began at a local pub with his family and there were "bar fights and drinking."

"He said, 'Do you want to get out of here?' And I was like, 'Uh, yeah, I do want to get out of here, John Kennedy,'" Shields said.

John F. Kennedy Jr. went on a date with Brooke Shields in Aspen, Colorado.

John F. Kennedy Jr. went on a date with Brooke Shields in Aspen, Colorado. (Photo by Brooks Kraft LLC)

She continued, "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."

Shields said she was starstruck by the moment.

John F. Kennedy Jr. during Labor Day Weekend in 1980.

John F. Kennedy Jr. during Labor Day Weekend in 1980. (Photo by Ron Galella/Ron Galella Collection)

"I froze though because he was so precious to me," she shared. "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."

She shared that she "had to get a cab home" which was "a little less chivalrous."

Brooke Shields was "madly in love" with John F. Kennedy Jr. since she was a young girl.

Brooke Shields was "madly in love" with John F. Kennedy Jr. since she was a young girl. (Photo by Jamie McCarthy)

When she saw Kennedy the following day, he "didn't look at me and he didn't talk to me."

"On the one hand, I was like, 'S---!' On the other hand, I was like, ‘Thank God … he showed his true colors,’" Shields admitted.

Kennedy married his wife, Carolyn Bessette, in 1996. The couple and Bessette's sister Lauren died in a plane crash in 1999.

John F. Kennedy Jr. and Carolyn Bessette wed in 1996 and died in a plane crash in 1999.

John F. Kennedy Jr. and Carolyn Bessette wed in 1996 and died in a plane crash in 1999. (Photo by Tyler Mallory/Liaison)

Shields also recently opened up about Tom Cruise, telling People magazine that the "Top Gun" star stopped sending her his exclusive Christmas cake after doing so for years.

She told the outlet she "had a good 10-year run" getting the cake the actor sent to his friends and family during the holiday season.

"I got the coconut cake every year, which I was very happy [about]," she said. 

Brooke Shields said Tom Cruise removed his ex-wife, Katie Holmes, from his Christmas card.

Brooke Shields said Tom Cruise removed his ex-wife, Katie Holmes, from his Christmas card. (Photo by Anthony Harvey)

Accompanied by the cake was a card each year from Cruise, his then-wife Katie Holmes and their daughter, Suri.

"It was from them and Suri [at first], so it was the three of them, and then soon it was no Suri and no Katie and just Tom," she revealed. "Then it went from just Tom for a while, but not every holiday. And then the cake stopped."

"Brooke Shields: Pretty Baby" debuted on Monday, where she opened up about her postpartum depression after the birth of her first kid, which ultimately led her to take antidepressants, much to the chagrin of Cruise.

Brooke Shields told Jay Leno in 2006 that Tom Cruise had apologized to her for his comments about antidepressants.

Brooke Shields told Jay Leno in 2006 that Tom Cruise had apologized to her for his comments about antidepressants. (Amy Sussman/Jeff Spicer)

In the documentary, Shields calls the 2005 incident, in which Cruise shared his feelings over the use of the medication, "ridiculous."

Cruise, who co-starred with Shields in the 1981 film "Endless Love," previously described psychiatric drugs as "dangerous," which he said is independent of the Church of Scientology's choice not to use "mind-altering psychotropic drugs."

Shields boldly responded to Cruise's initial comments, writing an op-ed piece for the New York Times and would later tell Jay Leno on "The Tonight Show" that Cruise apologized.

Janelle Ash is an entertainment writer for Fox News Digital.