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Reading: Leonardo DiCaprio and Gwyneth Paltrow Reunite Decades After He Apparently ‘Tried’ to Ask Her Out
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The Hollywood Ear > News > Leonardo DiCaprio and Gwyneth Paltrow Reunite Decades After He Apparently ‘Tried’ to Ask Her Out
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Leonardo DiCaprio and Gwyneth Paltrow Reunite Decades After He Apparently ‘Tried’ to Ask Her Out

News Room By News Room January 10, 2026
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The annual AFI Awards served as a rare reunion for Leonardo DiCaprio and Gwyneth Paltrow.

DiCaprio, 51, and Paltrow, 53, were spotted together at the Friday, January 9, awards show in Los Angeles, posing for a joint photo together. DiCaprio sported a classic black suit, while Paltrow opted for a white tank top over black bottoms.

DiCaprio and Paltrow, whose friendship dates back to the 1990s during the early days of their respective Hollywood careers, were last seen together at the 2005 Academy Awards when the One Battle After Another star was nominated for his performance in The Aviator.

Despite a longtime friendship, DiCaprio and the Goop founder never sparked a romance.

Related: Gwyneth Paltrow’s Dating History: Brad Pitt, Chris Martin and More

Conscious coupling! Gwyneth Paltrow has had her share of high-profile relationships over the years, dating fellow A-listers like Ben Affleck, Brad Pitt, Chris Martin and more. The Shakespeare in Love star began dating Pitt in 1994 after meeting him while on the set of the thriller Se7en. The couple got engaged in December 1996 only […]

“No, [I] never made out with Leo,” Paltrow claimed on a 2023 episode of the “Call Her Daddy” podcast. “He tried back in the day, but he was already, like, loose with goods from when he was 19.”

DiCaprio’s apparent rejection, however, didn’t hinder their friendship.

“He was vegetarian and he’d talk about how dirty meat is and how bad factory farming is,” Paltrow previously told the U.K.’s The Observer in 2013. “I haven’t eaten red meat in 20 years, and although Leo’s not totally responsible, he definitely planted a seed.”

She continued, “When I turned seriously macrobiotic, it coincided with my father having been diagnosed with cancer. I felt I could heal him by proxy.”

Gwyneth’s father, director Bruce Paltrow, was diagnosed with cancer in 1999 and died in 2002. He was 58.

“I got into wellness … actually because my father was diagnosed with cancer when I was about 25 years old,” Gwyneth recalled in a social media video shared in February 2024. “That started to catalyze my foray into understanding food, environmental toxins, food as medicine, alternative stuff like acupuncture. It started a long time ago — I don’t know, in the mid-’90s, because of my dad.”

Gwyneth is Bruce’s daughter with actress Blythe Danner, who has since become a parent herself. The Marty Supreme star shares daughter Apple and son Moses with ex-husband Chris Martin.

Gwyneth and Martin, 48, were married from 2003 to 2014, when they announced that they “consciously uncoupled.” They have since remained amicable coparents — even after Gwyneth moved on and married now-husband Brad Falchuk in 2018.

“If you’re saying you want to put your children first, then find a way not to do the thing where you’re cursing out the other one behind their back or dropping the kid at the end of the driveway,” Gwyneth said on “The World’s First Podcast” in April 2025. “It means a lot in separation and divorce.”

She added, “I think we have a really beautiful, big blended family. No, it is not perfect. But I actually don’t mind being the poster child for that, because if I feel like I could have impacted one kid’s experience, because their parents are like, ‘We can figure out a way to stay friends.’ It was worth it.”

As for DiCaprio, he has been in a relationship with model Vittoria Ceretti since 2023.

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