Leonardo DiCaprio is yet to become a father but he did show off his paternal side while on an outing with BFF Tobey Maguire’s teenage daughter and his young model girlfriend.
The 51-year-old Oscar winner – who is said to have supported Spencer Pratt’s Los Angeles mayoral run – was seen on a date night with girlfriend Vittoria Ceretti, 27, as they were joined by Tobey’s, 50, 19-year-old daughter Ruby Sweetheart Maguire.
DiCaprio showed his care for his pal’s daughter as he walked alongside her while holding the hand of his Italian supermodel girlfriend after dinner at Beefbar.
The trio chatted it up as they left the highly popular trendy luxury steakhouse as the actor and Ceretti towered over Ruby Sweetheart.
DiCaprio and Tobey have been best friends for a long time as they were known for being in the infamous ‘P**** Posse’ together.
The notorious Hollywood clique partied throughout the 1990s together as they were famous for their aggressive partying, womanizing, and exclusive club hopping.
Leonardo DiCaprio is yet to become a father but he did show off his paternal side while on an outing with BFF Tobey Maguire’s teenage daughter and his young model girlfriend
The 51-year-old Oscar winner – who is said to have supported Spencer Pratt’s Los Angeles mayoral run – was seen on a date night with girlfriend Vittoria Ceretti, 27
Among the roster were Maguire, David Blaine, Lukas Haas, Jay Ferguson, Josh Miller, Ethan Suplee and Scott Bloom.
To this day, DiCaprio is still known for his penchant of dating younger women as Ceretti is nearly half his age.
He has also dated several models and actresses in their 20s throughout the years including Gisele Bundchen, Blake Lively, Camila Mendes, Nina Agdal, Kelly Rohrbach, Bar Refaeli, Erin Heatheron, and Toni Garrn.
Tobey had kept a relatively low-profile in that regard until splitting from his age-appropriate jewelry designer wife, Jennifer Meyer, in 2020.
The Spider-Man actor was rumored to be dating influencer Lily Chee after they were spotted leaving Michael Rubin’s star-studded Hamptons White Party together in 2024, despite an almost thirty year age difference as he was 49-years-old and she was 20-years-old at the time.
Chee is currently 22-years-old and is less than three-years-older than Tobey’s daughter Ruby Sweetheart.
At the time, many called Chee a homewrecker as the allegations became so loud that Tobey’s ex Meyer was forced to speak out about the sighting, saying her ex was ‘as good of a guy as it gets.’
Many people think Chee met DiCaprio, and later Maguire, through a seasoned promoter.
They were joined by Tobey’s, 50, 19-year-old daughter Ruby Sweetheart Maguire
DiCaprio showed his care for his pal’s daughter as he walked alongside her while holding the hand of his Italian supermodel girlfriend after dinner at Beefbar
The trio chatted it up as they left the highly, popular trendy luxury steakhouse as the actor and Ceretti towered over Ruby Sweetheart
Ruby Sweetheart pictured with dad Tobey in Los Angeles back in December 2022
Dicaprio and Tobey (pictured in July 2017) have been best friends for a long time as they were known for being in the infamous ‘P**** Posse’ together
The notorious Hollywood clique partied throughout the 1990s together as they were famous for their aggressive partying, womanizing, and exclusive club hopping (Maguire and DiCaprio are pictured with Alex Polinsky in 1989)
Meanwhile, Maguire and Meyer first crossed paths in 2003 while he was on set of Seabiscuit at Universal Studios.
The former couple became engaged in 2006 and tied the knot the following year during a ceremony that was held in Hawaii.
Besides Ruby Sweetheart, the pair also share 17-year-old son Otis Tobias.
Tobey had kept a relatively low-profile in dating younger women until splitting from his age-appropriate jewelry designer wife, Jennifer Meyer, in 2020
The Amazing Spider-Man actor was rumored to be dating influencer Lily Chee after they were spotted leaving Michael Rubin’s star-studded Hamptons White Party together in 2024, despite an almost thirty year age difference as he was 49-years-old and she was 20-years-old at the time (pictrued)
Tobey, Ruby Sweetheart, and Meyer are seen in LA back in February 2016 with Tobey and Meyer’s son Otis Tobias
After nine years of marriage, the pair announced their separation in 2016 – and their divorce was finalized in 2020.
Maguire and Meyer said in a statement to People at the time of the split: ‘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 dated Ceretti since August 2023 as they have tried to keep their relationship as private as possible since.
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