Will Leonardo DiCaprio’s ex-girlfriends warn his supermodel new squeeze, 27, to run a mile? Six of them are HER best friends, says ALISON BOSHOFF
The news that actor Leonardo DiCaprio, 47 years old and a serial dater of young bikini models, is dallying with 27-year-old Gigi Hadid has raised eyebrows in Hollywood. After all, it’s rare for the star to break ‘Leo’s Law’ — and date a woman over the age of 25.
The pair were pictured for the first time at a Fashion Week party in New York, deep in conversation.
DiCaprio, wearing a peaked cap, appeared to be holding hands with the model who is 20 years his junior. Word is that they are ‘dating’ but ‘keeping it casual’.
So well known are DiCaprio’s dating preferences, that earlier this week he was the butt of a joke at the Emmy awards with actor Kenan Thompson saying on stage: ‘Twenty-six is a weird age in Hollywood. Young enough to play a High School student, but too old to date Leonardo DiCaprio.’
The news that actor Leonardo DiCaprio, 47 years old and a serial dater of young bikini models, is dallying with 27-year-old Gigi Hadid has raised eyebrows in Hollywood
It’s true that over the past two decades one young model has succeeded another in a never-ending model-merry-go-round.
But has an Oscar-winning star ever been so openly, and personally, derided?
And while model Gigi ponders whether their ‘fun’ and ‘casual’ dating might turn into a more serious romance, in truth she doesn’t need to listen to the chatter of the wider world to learn about her beau — as she can rely on plenty of advice from closer to home. And how well-informed it will be.
For, in a delicious twist, it turns out that Gigi is friends with no fewer than SIX of DiCaprio’s former girlfriends (all of them also models, of course).
They are Gisele Bundchen, Blake Lively, Erin Heatherton, Toni Garrn, Kelly Rohrbach and Nina Agdal, and they dated DiCaprio between 1999 and 2017. Sadly for DiCaprio, it’s hard to imagine that any of his exes will counsel Gigi that life as Leo’s plus one is much fun.
A source in the modelling world said: ‘He fishes in a small pond and the point was reached some time ago when all the models know him, and all the models have dated him. I would say that the situation is not really to his advantage.’
Gigi Hadid’s best friend among the tribe of his exes is actress and model Blake Lively — who has been a face of Dior and L’Oreal.
She and Gigi have been close since around 2014, when both were a part of singer Taylor Swift’s so-called girl squad.
A deep friendship has developed, and the pair have been seen hanging out at fashion shows, at the Met Gala Ball and at concerts and dinners in New York.
Lively, who is married to actor Ryan Reynolds and has just announced that she is pregnant with their fourth child, has given Gigi advice on raising daughter Khai, two.
Khai is Gigi’s child by former One Direction star Zayn Malik, from whom she split in October last year.
Both Gigi and Blake spoke about their bond in a recent interview with Vogue magazine. Blake said: ‘I told her you have to do what works for you. Gigi has a really special relationship with her fans, and I love how open she is on social media. I love seeing into her world . . . I’m grateful for what she shares but also understand whatever boundaries she chooses to set.’
For, in a delicious twist, it turns out that Gigi is friends with no fewer than SIX of DiCaprio’s former girlfriends (all of them also models, of course)
Last year, Blake wrote two posts on Instagram to celebrate her friend’s birthday, sharing a video clip of Gigi dancing with the fond caption: ‘Too bad you’re just super hot and no fun at all.’
She also shared a picture of herself with Gigi and her husband curled up on a couch with the caption: ‘I think you and I make a much better couple.’
Blake, 35, dated DiCaprio for five months between May 2010 and October 2011. They had met some time previously, when Blake was being considered for a role in The Great Gatsby, and were seen together at Disneyland, in Monte Carlo, in New York and in Sydney.
They appeared blissfully happy but broke up abruptly after Blake visited DiCaprio in Australia, where he was filming Gatsby.
Reports suggest that he cut her loose unexpectedly, and that she was heartbroken for a time.
He was then linked with model Madalina Ghenea whom he also met while in Australia.
Another former Leo love is blonde German model Toni Garrn. They were an item in 2013 and 2014, travelling to Cannes and Bora Bora — and seen kissing and cuddling in 2017, too, when he was ‘between models’ again.
Why did the romance end? Well, it all went south a few days after DiCaprio was spotted leaving the Art Basel show in Miami sporting a beard and a man bun and ‘with an entourage 20 women deep’.
It’s doubtful, then, that Toni will advise Gigi to go for it. Toni has known Gigi for years, indeed they became friends in 2014 at around the time that Toni first broke up with DiCaprio.
Spotted chatting together at the front row of a fashion show in 2015, Gigi was one of Toni’s biggest supporters when she launched a charity in 2016, aiming to support women and girls in Africa.
The Toni Garrn Foundation holds an annual ‘Supermodel Flea Market’ and Gigi has offered up to 100 garments a year for it. Both women are also Victoria’s Secret Angels, although Toni dropped out of the shows the year before Gigi put the famous wings on, saying that she was asked every year to lose more weight and she had simply found the demands impossible.
Toni found herself swiftly replaced in Leo’s affections by blonde swimsuit model Kelly Rohrbach (Kelly and Gigi also know each other, naturally).
Perhaps the most famous former flame is supermodel Gisele Bundchen. They got together in 1999, when she was only 18. DiCaprio apparently saw her on a catwalk and called her agency to get her phone number. Their six-year relationship has been his longest to date, with the couple splitting up in 2005.
However before the year was out he was with model Bar Rafaeli who, in looks, could be Gisele’s younger sister.
It must have been wounding. Gisele said in an interview that she wished DiCaprio well but it ended because she wanted to do ‘serious soul searching’ and he didn’t.
Although 15 years her senior, Gisele has been something of a mentor for Gigi, who was among those invited by Chanel to celebrate Gisele becoming the face of Chanel No 5 perfume in 2014.
By the time the two women were photographed together again four years later at the Met Gala Ball — both guests of Versace — they were friends and on close terms.
Gigi Hadid’s best friend among the tribe of his exes is actress and model Blake Lively — who has been a face of Dior and L’Oreal
When Gisele made remarks in an interview about how she couldn’t live her life like the younger generation of Insta models — which was perceived as a dig — she was quick to apologise to all of them.
The other ‘Leo’ models whom Gigi knows are friends through work — via advertising campaigns including one for Sports Illustrated.
Does it matter that he only dates models, and that they are all known to each other?
So far, it’s not put Gigi off. A source says: ‘Gigi and Leo have hung out multiple times and are into each other. Gigi thinks he’s a really cool guy.’
They have known each other socially for years — on the modelling party circuit — and the story is that they first ‘hung out’ at a party when private members’ club The Ned opened in New York in July. By then DiCaprio’s four-year relationship with model Camila Morrone was over.
Since that party he’s apparently been pursuing Gigi — being spotted with her in The Ned again in August.
The daughter of wealthy property developer Mohamed and super-ambitious Dutch model Yolanda, Gigi was raised to become a model and was pushed to diet and network her way to the top by her mother, who would tell her off for eating birthday cake, and discouraged an enthusiasm for basketball lest it lead to Gigi looking less feminine.
A source says: ‘Gigi is still fresh out of a very bad break up [with Zayn Malik] plus Leo has a reputation. We’ll see. But she’s a smart girl and will be looking before she leaps.’
And you have to wonder what view will be taken by Gigi Hadid’s formidable mother who has been married and divorced twice herself.
Calling herself ‘mama bear’, she is fully involved in the lives of daughters Gigi and Bella and sources indicate that Yolanda will be the gatekeeper if Gigi decides that the fling is going to mature into a true romance.
Her influence and presence in Gigi’s life was widely said to be what sparked the confrontation which ended her romance with Malik when daughter Khai was only one year old.
In October 2021 Yolanda dropped into the guest cottage at her farm where Malik was living with Gigi and their daughter without giving notice. In a confrontation which followed, Malik allegedly pushed Yolanda against a chest of drawers and shouted profanities.
A source says: ‘Gigi is still fresh out of a very bad break up [with Zayn Malik] plus Leo has a reputation. We’ll see. But she’s a smart girl and will be looking before she leaps’
He was charged with four counts of harassment, pleading guilty to one and no contest to the other three. He was subsequently sentenced to 360 days of community service, required to take anger management classes and to attend an anti-domestic violence programme.
He and Gigi separated shortly after the incident, but they have continued to raise their daughter together, and Malik even visits her and Khai at her Pennsylvania home.
Malik said in a statement that he had not struck Yolanda, but was choosing not to fight the charges in order to protect his daughter from the publicity which a court case would bring.
A friend in the modelling world says: ‘Gigi is a very mature 27. She spent years looking after Yolanda when she was ill with Lymes disease, and would drive her to hospital when she had flare-ups. Then she’s dealt with a lot with Zayn, and, of course, she is a mum too.
‘It wouldn’t surprise me if she was actually too grown up for Leo.’
Now there’s a thought.
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