Tobey Maguire ‘Partying Like a Rockstar’ With Friend Leonardo DiCaprio After Divorce

Leonardo DiCaprio may be all loved up with girlfriend Vittoria Ceretti , but his close buddy Tobey Maguire is keeping their womanizing flag flying by enjoying no frills fun and vowing he won’t get dragged into anything serious if he can help it, an insider exclusively reveals to Life & Style .

“Tobey and Leo have once again found themselves in tricky romantic waters,” the source says. “They've both invested a lot in the friendship in the years since Tobey's marriage fell apart, but I don't think anybody anticipated the extent to which Tobey would emulate Leo's famous lifestyle of chasing after women half his age and indulging in lengthy vacations like life is one big episode of Entourage .”

Leo and Tobey, both 49, met in the 80s while auditioning for the same roles as child actors.

“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,” Leo told Esquire in January 2014 about forcibly befriending the Spider-Man star as kids.

Tobey would eventually reciprocate his buddy’s enthusiasm for their blossoming friendship, especially after they first worked together filming This Boy’s Life in 1992.

The two became fast friends and, over the following decades, stuck by each other’s side through thick and thin.

While Tobey was tied down with wife Jennifer Meyer , Leo was notoriously playing the field, dating models and pop stars including Nina Agdal , Rihanna , Toni Garrn , Miranda Kerr and Blake Lively , to name a small fraction.

Tobey split from his wife – with whom he shares two children: son, Otis , and daughter, Ruby – in 2020.

The source continues: “ Tobey is a sweetheart around his kids and he would do anything for them, but when he's not playing single dad he’s partying like a rock star and cutting loose with no strings attached hookups.”

“He's having way too much fun enjoying his freedom and, of course, palling around with Leo and closely advising Leo on just about everything!”

As things heat up between the Titanic star and his current girlfriend, Vittoria, 26, the roles have flipped – and Tobey is now the devil on Leo’s shoulder!

“That's why it's a little hard to believe the speculation that Leo is really going to settle down with Vittoria, or anyone for that matter!” the source reasons.

“He's got Tobey in his ear extolling the virtues of an unattached lifestyle and playing wingman at a moment's notice.”

The Great Gatsby stars, who used to go by an untoward moniker, reportedly not of their own making, in their younger and more vulnerable years, The P--sy Possy, have been spotted yachting together – in St. Tropez in 2022, again in the south of France the following year, followed by more boating in Ibiza later in 2023 – shirts off and dad bods out.

“Even after 25 years on top,” the source says, “these guys still know how lucky they are and how much they can get away with if they're not tied down!”