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Leonardo DiCaprio and Gwyneth Paltrow were reunited publicly this week, nearly three decades after crossing paths early in their Hollywood careers.
The Oscar-winning actor and the Goop founder were photographed together at the AFI Awards, held on January 9 at the Four Seasons Hotel Los Angeles at Beverly Hills. Smiling for cameras, the two appeared relaxed as they posed side by side at the event.
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Their reunion comes years after Paltrow reflected on her early connection with DiCaprio during a 2023 appearance on the Call Her Daddy podcast. While discussing her dating history, she revealed that DiCaprio had expressed interest in her when they were both young actors, though nothing ever developed between them.
Archival photos place the pair together at industry events in the mid-1990s, when both were rising stars. At the time, DiCaprio was still in his teens, while Paltrow was in her early twenties.
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Since then, both have gone on to build high-profile personal and professional lives. Paltrow married television producer Brad Falchuk in 2018 and shares two children with her former husband, Coldplay frontman Chris Martin. She has previously spoken about prioritizing co-parenting and maintaining a healthy relationship with Martin following their separation.
DiCaprio, meanwhile, is currently dating Italian model Vittoria Ceretti, whom he has been linked to since 2023. The couple recently welcomed the New Year together in St. Barths alongside friends. In a 2025 interview with Vogue France, Ceretti described navigating a relationship with the actor as a learning experience, emphasizing trust and mutual understanding.
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The brief reunion of DiCaprio and Paltrow at the AFI Awards offered a nostalgic moment for fans, highlighting how two of Hollywood’s most enduring stars continue to cross paths decades into their careers.
