DiCaprio and Paltrow Reunite After 20 Years

A Rare Reunion at the AFI Awards

The annual AFI Awards brought together two Hollywood icons, Leonardo DiCaprio and Gwyneth Paltrow, for a rare reunion. The event, held on Friday, January 9, in Los Angeles, saw the pair posing for a joint photo. DiCaprio was seen in a classic black suit, while Paltrow opted for a white tank top paired with black bottoms.

Their friendship has spanned decades, dating back to the 1990s when both were just starting their careers in Hollywood. The last time they were seen together was at the 2005 Academy Awards, where DiCaprio was nominated for his role in The Aviator. Despite their long-standing friendship, the two never developed a romantic relationship.

In a 2023 episode of the "Call Her Daddy" podcast, Paltrow shared a candid moment about her past with DiCaprio. She said, "No, [I] never made out with Leo," adding, "He tried back in the day, but he was already, like, loose with goods from when he was 19." However, this did not affect their friendship.

A Shared Interest in Wellness

Paltrow also spoke about how DiCaprio influenced her lifestyle choices. In a 2013 interview with the U.K.’s The Observer, she mentioned, "He was vegetarian and he’d talk about how dirty meat is and how bad factory farming is." This conversation planted the seed for her own shift towards a healthier lifestyle.

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 passed away in 2002 at the age of 58.

In a social media video shared in February 2024, Paltrow reflected on how her father’s illness sparked her interest in wellness. "I got into wellness … actually because my father was diagnosed with cancer when I was about 25 years old," she said. "That started to catalyze my foray into understanding food, environmental toxins, food as medicine, alternative stuff like acupuncture."

A Family Legacy

Gwyneth is the daughter of Bruce Paltrow and actress Blythe Danner. Danner has since become a mother herself, and Gwyneth shares two children, Apple and Moses, with her ex-husband Chris Martin. The couple married in 2003 and divorced in 2014, though they have remained amicable co-parents.

"I think we have a really beautiful, big blended family," Paltrow said in an April 2025 episode of "The World’s First Podcast." "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."

DiCaprio’s Current Relationship

As for DiCaprio, he has been in a relationship with model Vittoria Ceretti since 2023. Their partnership has been relatively low-key, with both focusing on their respective careers and personal lives.