Leonardo DiCaprio reunites with longtime friend Tobey Maguire for a boys’ day out while girlfriend Vittoria Ceretti models in Paris for Fashion Week

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Leonardo DiCaprio reunited with his longtime pal Tobey Maguire in Venice Beach on Wednesday.

Leonardo DiCaprio, the actor known for Titanic, and Tom Holland, the star of Spider-Man, both aged 50, were seen spending the day together. This outing happened while Leonardo’s girlfriend, model Vittoria Ceretti, is in Paris attending Fashion Week.

For the occasion, Leonardo opted for a simple black top, beige trousers, and white trainers. 

He completed his understated outfit with a black baseball cap and used black sunglasses to protect his eyes.

Meanwhile, Tobey donned a black top with a comfy pair of joggers and grey trainers.

The two friends, who have known each other for more than 30 years, seemed happy and were laughing as they met.

Leonardo was seen out and about while his girlfriend was in Paris attending Fashion Week, along with many other celebrities.

Rumors of a romance between Vittoria and Leonardo began in August 2023 when they were spotted on an ice cream date in Santa Barbara. Then, the following month, the The Wolf of Wall Street star was seen at Milan Fashion Week showing his support for her.

Sometimes, people have spotted a ring on Vittoria’s wedding finger during her time with Leo, but sources close to them maintain that they are not engaged.

In March, the model expressed that it was ‘extremely annoying’ to be simply known as Leonardo DiCaprio’s girlfriend.

In an interview with Vogue France, she avoided mentioning Leonardo DiCaprio by name. Instead, she described him as a ‘very, very famous movie star’ and called his performance in Titanic ‘iconic’.

Despite this, Vittoria preferred to avoid publicly defining their relationship and explained that their connection is secure enough to prevent any feelings of jealousy.

She explained: ‘It’s a skill you develop over time. If your feelings are genuine, and you truly love one another, there’s no need to worry. That’s because love is protective and builds self-assurance.’

Only last month, the pair was seen going to dinner in West Hollywood to mark their second anniversary.

Vittoria was married to Italian DJ Matteo Milleri – one half of the Berlin-based duo Tale of Us – from 2020 to 2023.

Before Vittoria, DiCaprio dated Camila Morrone for five years but they split in 2022.

The famous actor was also rumored to be dating Gigi Hadid after sparks flew in September 2022. Leonardo DiCaprio has also been romantically connected to several other well-known women, including Gisele Bundchen, Bar Refaeli, Toni Garrn, Nina Agdal, and Blake Lively.

All of his girlfriends have been much younger than he is.

In a candid conversation, Leonardo explained: ‘Reaching the age of 50 brings a sense of wanting to be more truthful and prioritize what truly matters.’

It’s hard to picture what the future holds in the coming decades. I think of my mother, and she’s wonderfully direct – she always says what’s on her mind and doesn’t bother with pretense. She doesn’t waste time trying to put on an act or fake it.

Explaining why it’s important to be honest with your feelings, he said: ‘Being more upfront-even if it means a relationship might end, lead to disagreements, or cause you to go your separate ways-is a risk worth taking in any type of relationship.’

‘The personal, the professional — it’s that you don’t want to waste your time any more.

You really need to be more direct and open. It’s almost like a duty, considering you’ve lived most of your life already and have less time ahead than behind you.

In a recent interview with Esquire UK for their Autumn issue, the Hollywood actor stated he feels there’s “no time to waste” when it comes to dating, given his age. He explained that being truthful in relationships is a priority, even if it means risking losing a partner.

The actor, looking back on his dating life as an older man, explained that relationships sometimes ‘fall apart’ when he’s very direct about his desires. This comes after he’s faced criticism for primarily dating women in their twenties.

Leonardo also mentioned feeling like he’s lived most of his life already, and doesn’t anticipate many decades remaining, as he shared his thoughts about the future.

However, those rumors were quickly dismissed in February 2023. A source shared with the Daily Mail, ‘Leonardo DiCaprio is currently single and isn’t interested in the attention surrounding claims that he’s pursuing much younger women.’

The source added: ‘He wants a more serious and grown-up connection. It’s absurd, really, because he’s constantly associated with the youngest, most attractive woman wherever he goes.’

‘He wants to ditch this image once and for all and he is really bothered that this continues to follow him,’ they added.

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2025-10-02 11:04