Leonardo DiCaprio enjoyed a date night with Vittoria Ceretti — along with a surprise companion, Tobey Maguire’s daughter, Ruby Sweetheart Maguire.
The Oscar winner, 51, was spotted strolling through the streets of New York with his model girlfriend and his pal’s 19-year-old daughter after dinner at Beefbar.
In the photos shared by the Daily Mail, DiCaprio held hands with Ceretti as they walked alongside Ruby. The trio chatted it up as they left the trendy steakhouse.
Leonardo DiCaprio & Tobey Maguire’s Friendship Over the Years
Leonardo DiCaprio and Tobey Maguire have been friends for over 30 years. They first met in 1990 during the casting for “Parenthood,” where DiCaprio landed the lead teen role, and Tobey was handed a couple of lines.
At the time, DiCaprio spotted Tobey on a street in L.A. and recognized him as one of the kids from auditions.
“I literally jumped out of the car,” DiCaprio told Esquire in 2014. “I was like, ‘Tobey! Tobey! Hey! Hey!’ And he was like, ‘Oh, yeah — I know you. You’re that guy.’ But I just made him my pal. When I want someone to be my friend, I just make them my friend.”
GettyIn 2013, the Marvel star opened up about his friendship with DiCaprio. “[Leo and I] are like any other buddies. There’s a lot of laughing and chatting between us,” the “Spider-Man” actor told PEOPLE at the time. “We enjoy doing a lot of things we have in common, like basketball. We like to play and talk about basketball.”
Tobey added, “Leo and I have a lot of trust and respect for each other. We have a close friendship, and I definitely have an affection for Leo.”
Who Is Ruby Sweetheart Maguire?
GettyRuby Sweetheart is the eldest child of Tobey Maguire and jewelry designer Jennifer Meyer. The former couple welcomed their daughter on Nov. 10, 2006, during their nearly decade-long relationship. Ruby also has a younger brother, Otis Tobias Maguire, who was born in 2009.
In 2007, Tobey opened up about being a first-time dad. “I love my daughter … yeah, it’s definitely amazing!” the actor told reporters at a “Spider-Man 3” press day (via PEOPLE). “It’s like everybody says — all the clichés are true… It’s indescribable, and you just have to be there to understand it. You know, you don’t really get it until you’re there.”
Ruby has kept her personal life largely private, but a quick look at her social media reveals she’s attending Brown University.
In September 2025, Meyer shared several photos of herself dropping Ruby off at college.
“I love summer so much. I love my people (most of them not pictured),” Meyer wrote at the time. “Here are a few photos that I love from the last two months. Turns out dropping your daughter off at college really makes you cry a lot, but she’s good, so now I’m good.”
Tobey and Meyer first met in 2003 and got married in 2007. They separated in 2016 and finalized their divorce in 2020.
