Leonardo DiCaprio may not be a father yet, but he recently showcased his paternal instincts during an outing with his best friend Tobey Maguire's teenage daughter and his young model girlfriend. The 51-year-old Oscar winner, who is rumoured to have supported Spencer Pratt's Los Angeles mayoral campaign, was spotted on a date night with girlfriend Vittoria Ceretti, 27, accompanied by Tobey's 19-year-old daughter Ruby Sweetheart Maguire.
DiCaprio demonstrated his care for his friend's daughter as he walked alongside her while holding the hand of his Italian supermodel girlfriend after dining at Beefbar. The trio engaged in lively conversation as they left the trendy luxury steakhouse, with the actor and Ceretti towering over Ruby Sweetheart.
DiCaprio and Maguire have been close friends for decades, famously part of the notorious 'P***y Posse' clique that partied aggressively throughout the 1990s, known for their womanising and exclusive club hopping. The group included David Blaine, Lukas Haas, Jay Ferguson, Josh Miller, Ethan Suplee, and Scott Bloom.
To this day, DiCaprio is known for dating younger women, with Ceretti nearly half his age. He has previously dated models and actresses in their twenties, including Gisele Bundchen, Blake Lively, Camila Mendes, Nina Agdal, Kelly Rohrbach, Bar Refaeli, Erin Heatherton, and Toni Garrn.
Maguire had kept a relatively low profile in this regard until his split from age-appropriate jewellery designer wife Jennifer Meyer in 2020. The Spider-Man actor was rumoured to be dating influencer Lily Chee after they were spotted leaving Michael Rubin's Hamptons White Party together in 2024, despite a nearly 30-year age gap; he was 49 and she was 20 at the time. Chee, now 22, is less than three years older than Maguire's daughter Ruby Sweetheart. The allegations led to Meyer speaking out, calling her ex 'as good of a guy as it gets.'
Maguire and Meyer first met in 2003 on the set of Seabiscuit at Universal Studios. They became engaged in 2006 and married the following year in Hawaii. Besides Ruby Sweetheart, they share a 17-year-old son, Otis Tobias. After nine years of marriage, they announced their separation in 2016, with their divorce finalised in 2020. In a joint statement to People, they said: 'After much soul searching and consideration we have made the decision to separate as a couple. As devoted parents, our first priority remains raising our children together with enduring love, respect and friendship.'
Meanwhile, DiCaprio has been dating Ceretti since August 2023, and they have tried to keep their relationship as private as possible.
