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The news that actor Leonardo DiCaprio, 47, and a serial dater of young bikini models, is dating 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 25.
The pair were first pictured at a Fashion Week party in New York, deep in conversation.
DiCaprio, wearing a cap, seemed to go hand in hand with the model 20 years younger. They are rumored to be “dating” but “keep it casual”.
DiCaprio’s dating preferences are so well known that earlier this week he was the butt of an Emmy joke with actor Kenan Thompson saying onstage, “Twenty-six is a weird age in Hollywood. Young enough to play high school, but too old to date Leonardo DiCaprio.”
The news that actor Leonardo DiCaprio, 47, and a serial dater of young bikini models, is dating 27-year-old Gigi Hadid has raised eyebrows in Hollywood
It is 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 mocked so openly and personally?
And while model Gigi wonders if their “fun” and “casual” dating could turn into a more serious romance, in reality she doesn’t need to listen to the wider world’s chatter to learn more about her beauty — there she can rely on lots of advice from closer to home. And how knowledgeable it will be.
Because in a delightful twist, it turns out that Gigi is friends with no fewer than SIX of DiCaprio’s ex-girlfriends (all of them models too, of course).
They are Gisele Bundchen, Blake Lively, Erin Heatherton, Toni Garrn, Kelly Rohrbach and Nina Agdal, and they were in a relationship with DiCaprio between 1999 and 2017. Unfortunately for DiCaprio, it’s hard to imagine any of his exes advising Gigi that life as leo’s plus one is a lot of fun.
A modeling source said: ‘He’s fishing in a small pond and it got to the point some time ago where all the models know him and all the models have dated him. I’d say the situation isn’t really in his favour.’
Gigi Hadid’s best friend among the tribe of his exes is actress and model Blake Lively – who was a face of Dior and L’Oréal.
She and Gigi have been close since about 2014, when both were part of singer Taylor Swift’s so-called girl group.
A deep friendship has developed and the couple has been spotted at fashion shows, the Met Gala Ball and at concerts and dinners in New York.
Lively, who is married to actor Ryan Reynolds and just announced she is pregnant with their fourth child, has given Gigi some advice on raising daughter Khai, two.
Khai is Gigi’s child of former One Direction star Zayn Malik, from whom she split in October last year.
Both Gigi and Blake spoke about their band in a recent interview with Vogue magazine. Blake said, “I told her to do what works for you. Gigi has a very special relationship with her fans and I love how open she is on social media. I love looking into her world. . . I am grateful for what she shares, but also understand what boundaries she chooses.’
Because in a delightful twist, it turns out that Gigi is friends with no fewer than SIX of DiCaprio’s ex-girlfriends (all models too, of course)
Last year, Blake wrote two posts on Instagram to celebrate her boyfriend’s birthday, sharing a music video of Gigi dancing with the precious caption, “Too bad you’re just super hot and not fun at all.”
She also shared a photo of herself with Gigi and her husband curled up on a couch with the caption, “I think you and I are a much better couple.”
Blake, 35, dated DiCaprio for five months between May 2010 and October 2011. They had met some time before, when Blake was being considered for a role in The Great Gatsby, and were seen together at Disneyland, Monte Carlo, New York and Sydney.
They seemed overjoyed, but broke up abruptly after Blake visited DiCaprio in Australia, where he was filming Gatsby.
Reports suggest he let her go unexpectedly and she was heartbroken for a while.
He was then associated with model Madalina Ghenea, whom he also met in Australia.
Another former Leo crush is blonde German model Toni Garrn. They were an item in 2013 and 2014, traveling to Cannes and Bora Bora – and also saw him kissing and cuddling in 2017, when he was “between models” again.
Why did the romance end? Well, it all went wrong a few days after DiCaprio was seen leaving the Art Basel show in Miami with a beard and a man bun and “with an entourage 20 women deep.”
So it’s doubtful that Toni will advise Gigi to go for it. Toni has known Gigi for years, indeed, they became friends in 2014 around the time Toni first broke up with DiCaprio.
Gigi, who was chatting together in the front row of a fashion show in 2015, was one of Toni’s biggest supporters when she launched a charity in 2016 focused on supporting women and girls in Africa.
The Toni Garrn Foundation holds an annual ‘Supermodel Flea Market’ and Gigi has offered up to 100 items of clothing per year for it. Both women are also Victoria’s Secret Angels, although Toni quit the shows the year before Gigi put on the famous wings, saying that every year she was asked to lose more weight and that she had simply found the demands impossible.
Toni found herself quickly replaced in Leo’s affections by blonde swimsuit model Kelly Rohrbach (Kelly and Gigi know each other, of course).
Perhaps the most famous former flame is supermodel Gisele Bundchen. They met in 1999, when she was only 18. DiCaprio apparently saw her on a runway and called her agency to get her phone number. Their six-year relationship is the longest to date, with the couple breaking up in 2005.
But before the year was up, he was with model Bar Rafaeli, who in appearance could be Gisele’s younger sister.
It must have been an injury. Gisele said in an interview that she wished DiCaprio the best but it ended because she wanted to do “serious soulsearching” and he didn’t.
Although she is 15 years her senior, Gisele has been a kind of mentor to Gigi, who was one of 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 at the Met Gala Ball four years later – both guests of Versace – they were friends and bonded.
Gigi Hadid’s best friend among the tribe of his exes is actress and model Blake Lively – who was a face of Dior and L’Oréal
When Gisele made comments in an interview about how she couldn’t live her life like the younger generation of Insta models – what was seen as a dig – she quickly apologized to all of them.
The other “Leo” models Gigi knows are friends from work – through advertising campaigns, including one for Sports Illustrated.
Does it matter that he only dates models, and they are all known to each other?
So far, it hasn’t deterred Gigi. A source says: ‘Gigi and Leo have hung out several times and are crazy about each other. Gigi thinks he’s a really cool guy.’
They’ve known each other socially – in the modeling party circuit – and the story goes that they first “hanged out” at a party when the private members club The Ned opened in New York in July. By this time, DiCaprio’s four-year relationship with model Camila Morrone was over.
He’s apparently been chasing Gigi since that party – spotted with her again in The Ned in August.
The daughter of wealthy property developer Mohamed and super-ambitious Dutch model Yolanda, Gigi was raised to be a model and forced by her mother to diet and network to the top, who would tell her she ate birthday cake, and discouraged an enthusiasm for basketball, otherwise Gigi would look less feminine.
A source says: ‘Gigi is still fresh from a very bad breakup’ [with Zayn Malik] plus Leo has a reputation. We will see. But she’s a smart girl and will look before she jumps.’
And you have to wonder what stance will take the formidable mother of Gigi Hadid, 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 the affair will develop into a true romance.
Her influence and presence in Gigi’s life is said to have sparked the confrontation that ended her romance with Malik when daughter Khai was just one year old.
In October 2021, Yolanda invaded the guest house on her farm where Malik lived with Gigi and their daughter without notice. In a confrontation that followed, Malik allegedly pushed Yolanda against a chest of drawers and yelled curses.
A source says: ‘Gigi is still fresh from a very bad breakup’ [with Zayn Malik] plus Leo has a reputation. We will see. But she’s a smart girl and will look before she jumps’
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, had to take anger management classes and participate in a domestic violence program.
He and Gigi broke up 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 did not hit Yolanda, but chose not to sue in order to protect his daughter from the publicity that a lawsuit would bring.
A modeling friend says, “Gigi is a very mature 27-year-old. She cared for Yolanda for years when she had Lymes disease, and would take her to the hospital if she had flare-ups. Then she has had a lot to do with Zayn, and of course she is also a mother.
“I wouldn’t be surprised if she was actually too grown up for Leo.”
Now there is a thought.