He’s been stunning us with his acting chops since childhood, earning his first Oscar nomination at just 19, before going on to receive seven more, and – of course – winning one in 2015. But while Leonardo DiCaprio’s career has matured like the finest Cabernet over the past four decades, the same cannot be said for his dating life. He may be getting older, but his revolving door of girlfriends never seem to reach their late 20s before he moves on, never settling down.

Indeed, the actor has long held a reputation for dating women aged 25 and younger – leading to a dichotomy in the public eye where he’s simultaneously lauded for his career, and teased for his dating. His girlfriend of one year, model Vittoria Ceretti, is no exception. Though she recently broke through his alleged age ceiling, having turned 26 in June, the fact she was born the same year Titanic was released elicits something of a sinking feeling among some of us and has us all wondering: when will Leo let go?

Now, as the celebrated actor turns 50 next week, we’re told his friends and family are starting to raise their concerns more vocally. It may have been OK to play the perennial playboy throughout his 20s, 30s, and 40s – but, now that he’s reached his milestone birthday, something’s got to give. And, like all successful 50 year olds, when it comes to their penchant for dating younger women, it’s up to his beloved mum, Irmelin, to knock some sense into him. 

“She’s telling him flat-out to pull himself together, grow up, and stop messing with these girls’ heads,” says an insider close to the superstar actor, who’s long credited both Irmelin and his dad, George, for supporting and facilitating his Hollywood dreams from day dot. “George tries not to interfere too much in his son’s life, but he’s known to find it very puzzling and bizarre that Leo’s still breaking hearts as he closes in on 50. Irmelin is more direct. She’s getting tired of him introducing her to someone and then two minutes later replacing them with some other 25 year old. Moving forward, his family only want to know about his love life when he’s put a ring on someone’s finger. They want to see him married and with a family of his own, and they’re telling him it’s time to grow up and stop being a lothario. It’s embarrassing for them to see.” 

There’s no denying that the actor’s pattern of dating younger women is just a little tacky for some and has people worrying. The question is will Leo ever change his ways?

Since meeting Vittoria last summer in Europe (back when, crucially, she was still 25) the duo has apparently enjoyed a hot and heavy romance ever since, with one insider saying Leo is ready to “hang up his lothario ways” for the Italian model. But many in his inner circle are still wondering how long it will be before he’s back to his old lust for younger love. His last long-term relationship, with model Camilla Morrone, ended in August 2022 after five years together – soon after she turned 25. Previous girlfriends – including Gisele Bundchen, Bar Rafaeli and Blake Lively – were all under 25 when he dated them. And though he’s made some exceptions in the past, reportedly briefly dating Gigi Hadid when she was over the hill at 28, the facts remain that Leo’s been playing The Generation Game for decades. 

Still, there’s something about reaching half a century that makes many people take stock of where they are in life, and where they want to go from here. As an only child, we’re told Leo’s parents are fed up of seeing him gallivanting on private boats with young women, and are desperate to see him slow down – and maybe even give them a grandchild or two in the future. When you’re an Oscar-winning A-lister, you have very few people in life telling you off, and even fewer you’re willing to listen to. But, according to our source, if there are any two people he’ll accept advice from, it’s his parents. And this time, they’re not keeping quiet. 

“Leo is super tight with his mum and dad,” says our source. “He’s always taken great pride in looking after them since getting rich and famous. Still, they just want the best for their son, and would like Leo to get serious about his future. It’s time for him to stop fooling around with these girls and just pick one. For a long time, they let it slide that he had a revolving door of girlfriends aged 25 and under. He’s their son and they love him, but they’re getting annoyed now and would like to see him make some major changes.”

Let’s not forget, for every perennial bachelor who’s unwilling to change the track, there’s a reformed George Clooney who’s breaking the mould. Famously, George was just as incorrigible as Leo when it came to his choices in the love department and his resistance to settling down for good. But after meeting Amal Clooney (née Alamuddin), everything changed. They got married when George was 53, and went on to have two children together, twins Ella and Alexander, seven. So, maybe turning 50 will give Leo the push he needs to start widening his remit – or, at least, increase his age limit on Raya. 

Whether he does change his tune or not, one truth remains: Leo may be getting too old to keep dating women in their early 20s, but he’ll never, ever, be too old to listen to his Mum.