Leonardo DiCaprio, 51, shows off paternal side with BFF Tobey Maguire’s daughter, 19, and girlfriend Vittoria Ceretti, 27, on night out in NYC

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Leonardo DiCaprio doesn’t have children of his own yet, but he recently demonstrated a caring side while spending time with his close friend Tobey Maguire’s teenage daughter and Maguire’s girlfriend, who is a model.

Oscar winner Joaquin Phoenix, 51, was spotted on a date with his girlfriend, Vittoria Ceretti, 27. They were joined by Tobey Maguire’s 50-year-old daughter, Ruby Sweetheart Maguire, 19, making it a family outing. Phoenix is rumored to have previously supported Spencer Pratt’s campaign for mayor of Los Angeles.

Leonardo DiCaprio was spotted walking with his girlfriend, a well-known Italian model, and a friend’s daughter after having dinner at Beefbar. He held his girlfriend’s hand and walked beside the daughter, appearing to make sure she was safe and comfortable.

The three friends were talking and laughing as they exited the very popular, upscale steakhouse, with the actor and Ceretti noticeably taller than Ruby Sweetheart.

Okay, so, you HAVE to know, Leo and Tobey? They’ve been inseparable forever! It’s legendary – they were part of this group back in the day, the ‘P Posse,’ and honestly, it just proves how close they are. It’s a total iconic friendship, seriously!

Throughout the 1990s, a well-known Hollywood group gained a reputation for their wild parties, relationships with many women, and frequenting exclusive nightclubs.

The group included actors Maguire, Lukas Haas, and Josh Miller, along with illusionist David Blaine, and musicians Jay Ferguson, Ethan Suplee, and Scott Bloom.

Even now, Leonardo DiCaprio is still recognized for his tendency to date women much younger than himself, as his current partner is almost half his age.

Over the years, he’s been linked to a number of models and actresses in their twenties, including Gisele Bündchen, Blake Lively, Camila Morrone, Nina Agdal, Kelly Rohrbach, Bar Refaeli, Erin Heatherton, and Toni Garrn.

Tobey generally stayed out of the spotlight when it came to his personal life until he separated from his wife, jewelry designer Jennifer Meyer, in 2020.

In 2024, rumors circulated that Spider-Man actor Tom Holland was dating influencer Lily Chee. The two were seen leaving Michael Rubin’s popular Hamptons White Party together, sparking conversation due to their significant age difference – he was 49, and she was 20 at the time.

Chee is 22 years old, and only a few years older than Tobey’s daughter, Ruby Sweetheart.

When the rumors surfaced, many accused Chee of being responsible for the breakup. The situation escalated to the point where Tobey’s former partner, Meyer, publicly defended her ex, describing him as a genuinely good person.

Many people think Chee met DiCaprio, and later Maguire, through a seasoned promoter.

Maguire and Meyer met for the first time in 2003 on the set of the movie Seabiscuit at Universal Studios.

The couple got engaged in 2006 and married in Hawaii the next year.

Besides Ruby Sweetheart, the pair also share 17-year-old son Otis Tobias. 

The couple married for nine years before separating in 2016, and their divorce became final in 2020.

Maguire and Meyer announced in a statement to People that they had decided to separate after careful consideration.

We are committed parents, and our main focus is to raise our children with lasting love, respect, and a strong bond of friendship.

Leonardo DiCaprio has been dating Vittoria Ceretti since August 2023, and they’ve largely kept their relationship out of the public eye.

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2026-05-28 21:34