Leonardo DiCaprio and Tobey Maguire have one of the most long-lasting relationships in the industry. One of the reasons behind their strong relationship is their similar personal background which deepened their bond. Not just their personal life but their acting career also started in a similar fashion when they debuted in the industry as a kid.

Leonardo DiCaprio and Tobey Maguire
Leonardo DiCaprio and Tobey Maguire

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Their bonding is still strong which is why they always stick together during parties or outings. Having a history of dating many women, DiCaprio has often taken charge of introducing his friend to social circles. However, things often go unexpected as something similar happened during their outing earlier this year.

Tobey Maguire Failed to Attract Ladies During His Nightout With Leonardo DiCaprio

Tobey Maguire
Hollywood actor Tobey Maguire

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The 47-year-old actor, Tobey Maguire in February this year was partying together with his longtime friend Leonardo DiCaprio in the VIP section of nightclub MainRō restaurant and supper club in Hollywood.

A source at that time told PageSix, “Tobey and Leo came to the club together for a boys’ night out.”

The source added that the Spider-Man star was “on the prowl and Leo was his wingman.”

With the Titanic star’s help, the former was introduced to “three different blondes.” However, the source added, “Even with Leo’s help, Tobey couldn’t land a girl.”

As per the outlet, none of the ladies introduced to the former “seemed interested” in the actor even though he was quite in the limelight after being starred in the then-latest Spider-Man: No Way Home movie.

A Brief Note on Tobey Maguire’s Relationship

Tobey Maguire
Tobey Maguire as Spider-Man in the MCU

Also Read: Elizabeth Banks Tortured Tobey Maguire on the Sets of Spider-Man

The Great Gatsby star had been romantically involved with jewelry designer Jennifer Meyer since 2003. They got married in 2007 sharing two children, Ruby and Otis.

After nine years of their marriage, they announced their separation in 2016. The designer filed for divorce two years ago.

He was also linked with model Tatiana Dieteman in 2018. They maintained a low-key relationship ahead of the COVID-19 pandemic however their relationship was short-lived as they got separated last year.

Since then, the actor has been embracing the single life and was recently spotted at DiCaprio’s 48 birthday bash in Beverly Hills. He was spotted with a mystery brunette woman in the evening.

However, a few hours later, he was spotted with a blonde woman during his dinner plan at the rooftop seafood restaurant Catch LA.

Source: PageSix

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