The late Playboy Magazine mogul Hugh Hefner may spring to mind when it comes to celebrity men who seem to be almost constantly surrounded by bevvies of younger women – but one celeb really has topped the list of Hollywood’s most ‘bachelor-like’ singletons over the past couple of decades.
However, in a breaking story that is bound to send shockwaves through Hollywood and backstage at the Victoria’s Secret fashion shows, a source tells us that this handsome A-lister is ready to quit his dating days for good.
Yes, it’s Leonardo DiCaprio, 50 - Hollywood’s most notorious bachelor, who can be generally found acting, campaigning, or aboard a yacht surrounded by half a dozen bikini-clad models.
That is until he met his current love, model Vittoria Ceretti, 26, who the Once Upon a Time…In Hollywood actor has been dating for two years this August.
Now our insider says, ‘Leonardo DiCaprio is getting incredibly serious with model Vittoria Ceretti and pals predict an engagement right around the corner.
‘It’s a big deal for him to finally see Vittoria as marriage material. Leo doesn’t want to wind up an old bachelor and that’s where he’s headed if he doesn’t do something about it soon. Leo’s given considerable thought to marrying Vittoria and he’d like to sooner rather than later.
‘He’s always been known as Hollywood’s biggest bachelor but at his age, it’s started to become not a good thing – he’s ready to quit that title.’
Leo has long been famed for his colourful dating history, which has seen him date some of the world’s most beautiful women.
His tendency to date women under 25 only has also spawned several memes, with fans calling the actor’s ‘rule’, ‘Leo’s law’.
However, after meeting Vittoria, who was 26 at the time they met in Milan in 2023, Leo’s latest romance has been an exception to the rule from the very first.
And with insiders letting slip at the time that the Oscar winner had become ‘smitten’ within just a few months, our source now says this is the first time that Leo hasn’t had cold feet over the thought of settling down.
Vittoria, too, is said to have been telling friends that she’s ready to take her real life ‘Mr Big’ off the market.
The insider says, ‘There’ve been signs for a while that they’re moving in that direction. She has let it be known very loudly that marriage is the end game for her and she won’t stick around forever waiting.
‘For the first time ever Leo has said that he’s aiming for that too. That came as a big shock to people because he’s always dodged making those sorts of promises.’
They add, ‘Nearly everyone in Leo’s life has been imploring him to settle down for years but as everyone knows, he’s deliberately held off, it’s always been a no-go. So it’s quite exciting for his loved ones to see him finally warming to the idea.’
Leo became a worldwide heartthrob overnight when he played history’s most tragic romantic hero in Romeo and Juliet in 1996, and, just a year later, the baby-faced actor secured his ultimate pin-up status when he starred in Titanic, during which his steamy sex scene with Kate Winslet would go down in film history.
At the time, the up and coming actor was already dating Victoria’s Secret model Bridget Hall, whom he split with in the mid ‘90s, when he struck up a rumoured romance with model Naomi Campbell.
His extensive dating history is also rumoured to include relationships and brief romances with Helen Christensen, Eva Herzigova, Blake Lively, Miranda Kerr, Rihanna, and Gigi Hadid.
It was widely assumed back in 2022 that Leo was ready to quit his single days after dating model and Al Pacino’s step daughter Camilla Morrone, 20, for five years – his longest relationship after Gisele Bundchen, whom he dated for four years in the early noughties.
But now the source says Leo is finally ready to commit and, even more delighted than Vittoria is his biggest fan, his mum Irmelin Indenbirken, who the insider says, at 82, is hoping for grandchildren.
They say, ‘Leo has taken a lot longer than most men to mature but it’s now looking like he will be one of those late bloomers, rather than a terminal bachelor, which is a massive relief for his mum, who really wants to see him have a child.’
Not only has Leo overhauled his romantic life, but fans have noticed the actor’s noticeably trimmed down figure, which he has been showing off on trips to Europe with Vittoria, with the couple photographed in Spain enjoying a double restaurant date with friends last week.
And with insiders revealing that Vittoria is ‘enjoying’ her man’s new physique, our source says the model, who has appeared on the cover of Vogue worldwide 24 times, has been a ‘great influence’ on the actor.
They add, ‘He’s slimmed down and gotten in much better shape since they started dating. He’s partying way less as well. Vittoria's quite focused on work and something of a homebody and that’s rubbed off on Leo.
‘They still party at times and have plenty of fun but he doesn’t have the same constant need to be out and about, the FOMO is gone with Vittoria’.
The Fear of Missing Out, however, is still said to be going strong when it comes to the friendly banter Leo shares with his close pal Bradley Cooper, who is also rumoured to be set to pop The Question to girlfriend (and Leo’s ex) Gigi Hadid any day now.
Rumours reached fever pitch last month when Gigi was spotted wearing a ring on her wedding finger during her 30th birthday celebrations, where she and Bradley, 50, were photographed kissing.
And now our source says Leo is determined not to just follow suit, but wants to be the first of the famous bachelors to walk up the aisle.
They say, ‘There is no doubt that Leo has heard the rumours of Bradley proposing to Gigi, which to him means the heat will be on him.
‘Of course he knows he’s making the right decision but a little nudge from Bradley could be just what he needs. He doesn’t want to be seen as Hollywood’s Last Bachelor Standing.’