That Leonardo DiCaprio would be in New York for Fashion Week is like the punchline to a familiar joke.
The actor, who is 47, has dated a string of bikini models all under the age of 25 for nearly three decades; Leo’s Law with regards to his partners’ youth has in fact become so established that one recent Sports Illustrated party was virtually a gathering of past and future girlfriends.
And now he’s drawn to supermodel Gigi Hadid.
At 27, and as a mom, she is a couple of years outside his usual age range and has life experience which no former girlfriends have had. But she is around half his age, blonde and gorgeous, so in many ways, remains true to type.
In fact, Gigi not only boasts the same enviable assets as all of Leo’s former partners, she also has close links with many of them – which may be at least one of the reasons why sources tell me that she is reluctant to start a romance with the actor.
Among DiCaprio’s line-up of lithe ex-girlfriends includes Gigi’s close friend Blake Lively, whom she has known for many years, as well as several model colleagues and catwalk pals, such as Nina Agdal, Erin Heatherton, and Toni Garrn.
After weeks of speculation about a blossoming romance between Leonardo DiCaprio, 47, and Gigi Hadid, 27, DailyMail.com published the exclusive first pictures of the pair enjoying a night out together in New York City on Monday night
At 27, and as a mom, Gigi is a couple of years outside of DiCaprio’s usual age range and has life experience which no former girlfriends have had. But she is around half his age, blonde and gorgeous, so in many ways, remains true to type
Gigi not only boasts the same enviable assets as all of Leo’s former partners, she also has close links with many of them – which may be at least one of the reasons why sources tell me that she is reluctant to start a romance with the actor
Gigi’s entanglement in DiCaprio’s web of former love interests may well be one of the reasons that he was drawn to her in the first place; ironically, it could also be one of the key reasons that she is hesitant to get involved with the star.
Gigi Hadid’s many entanglements in Leo DiCaprio’s web of women
If Gigi Hadid is wondering about what Leonardo DiCaprio would be like as a boyfriend she has plenty of pals to call on who can fill her in. In fact she’s on friendly terms with at least six of his ex girlfriends.
GISELE BUNDCHEN (1999-2005)
Gisele and Gigi cozied up to each other at the Met Gala Ball in 2018.
BLAKE LIVELY (2011)
Gigi became friends with actress Lively via mutual pal Taylor Swift. In 2019 she wrote on Instagram, ‘It’s this Queen’s birthday week and I just want to say how grateful and lucky I am to have a friend like you, B. You are a real one and inspire me in so many ways. I will only be able to thank you enough by making you endless oatmeal griddle cakes and training your children to be world class disposable-camera photographers. I love you! Wishing you every blessing.’
ERIN HEATHERTON (2012)
Gigi knows Erin Heatherton – both modelled for Sports Illustrated and attended a party to launch the swimsuit issue in New York in 2016. They were also in a modelling campaign together in 2013.
TONI GARRN (2013-2014)
Gigi and Toni sat on the front row of the Diesel show at New York Fashion week in 2015.
KELLY ROHRBACH (2015)
Gigi and Kelly did a shoot for Sports Illustrated – vintage shopping in Nashville – in 2015.
NINA AGDAL (2016-2017)
Gigi was pictured with Nina at Sports Illustrated events in 2015 and 2016.
As our exclusive pictures reveal, the pair have been hanging out together at parties – with our images showing them looking cozy at a bash thrown by DiCaprio’s friend Richie Akiva in Soho on Monday night.
Unusually, however, Leo’s inner circle has been sounding a note of caution. One insider told E!, ‘He’s enjoying being single,’ adding that the couple are ‘not exclusive… neither of them want a relationship.’
The source adds: ‘Gigi and Leo have hung out multiple times and are into each other. Gigi thinks he’s a really cool guy.’
Hadid and DiCaprio 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 Akiva’s private members club and hotel, The Ned, opened in New York in July.
By then DiCaprio’s four year relationship with model Camila Morrone was over.
Since then he’s been apparently pursuing Gigi – and was spotted with her at The Ned again in August.
Both, though, have been seen out without each other over the past few months, with DiCaprio on the scene most nights over the summer with a posse of male pals in New York and Malibu and Gigi going to several fashion week parties without him.
And the story behind the scenes is surprising – as there is a suspicion that Gigi actually isn’t all that into Leo.
After many years of being one of the most eligible bachelors in Hollywood, perhaps his famous pulling power is fading.
A source tells me: ‘Gigi is still fresh out of a very bad break up (with One Direction star Zayn Malik) plus Leo has a reputation. We’ll see. But she’s a smart girl and will be looking before she leaps.’
A week ago, US Weekly reported DiCaprio has ‘his sights set on Gigi,’ but ‘she doesn’t want to be romantic with [him] right now.’
This would explain why his friends are keen to push the story that this is strictly casual – because a middle-aged A-lister being turned down by a model precisely 20 years his junior is not a good look.
In truth, his love life has become an embarrassment – a joke on a global scale.
Ricky Gervais roasted him in 2020 when talking about the Quentin Tarantino film Once Upon a Time in Hollywood at the Golden Globes. ‘It’s almost three hours long – it’s an epic. Leonardo DiCaprio attended the premiere and by the end his date was too old for him.’ The audience – DiCaprio’s friends and peers – laughed and Gervais added: ‘Even Prince Andrew’s like, ‘Come on, mate, you’re nearly 50, son.’
Actress Rebel Wilson returned to the joke at the BAFTAs in London in March. She said to 20-year-old Emilia Jones: ‘I’ll give you the award for the person in the crowd Leonardo DiCaprio would find most attractive… He does like them young.’
Supermodel Gisele Bundchen, now 42, and DiCaprio dated on and off for six years between 1999 and 2005 (left). Then, in 2018, the model was seen cozying up to Gigi on the red carpet at the Met Gala (right)
DiCaprio dated Blake Lively, now 35, back in 2011 (left); the actress has been close friends with Gigi for several years after the pair were introduced by mutual pal Taylor Swift
In 2012, DiCaprio had a brief romance with Erin Heatherton (left), now 33, who has not only modelled for Sports Illustrated like Gigi, the pair also appeared in a modeling campaign together in 2013 (right)
After Erin, DiCaprio began dating another model, Toni Garrn (left), now 30, whom Gigi was seen getting close with while they sat front row at the Diesel show at New York Fashion week in 2015 (right)
DiCaprio debuted his romance with Baywatch actress and model Kelly Rohrbach (left), now 32, in 2015; that same year, Kelly and Gigi did a shoot for Sports Illustrated, which saw them vintage shopping together in Nashville (right)
DiCaprio’s former flame Nina Agdal, now 30, attended several Sports Illustrated events with Gigi in 2015 (right) and 2016 – the same year she began dating the actor (left)
The fact is that what looked like a great Brat Pack party when Leo was aged 25 himself now appears creepy as he nears 50.
Friends say that he came closest to marriage with model Bar Rafaeli over ten years ago.
Not long afterwards he told Parade magazine: ‘That time will come when that time comes. The truth is, you can’t predict marriage. You can’t plan it. It’s just going to happen when it happens.’
DiCaprio’s budding romance with Gigi comes just weeks after he split from his ex-girlfriend Camila Morrone, who just turned 25. He was first introduced to Camila back in 2008, when she was only 12 through his longtime friend Al Pacino
That’s a view which is not likely to impress Gigi’s formidable mother, Yolanda – who has been married and divorced twice – and Yolanda is the woman who he will need to impress if the blossoming attraction to Gigi is ever to mature into a full-blown romance.
An ex-model, who calls herself ‘mama bear’, she is very involved in the lives of both her model daughters Gigi and Bella and sources indicate that Yolanda will be the gate keeper if Gigi decides that she wants to bring Leo home. In other words, he’ll need to pass her ‘sniff test’ as a beau.
She’s said that she follows all her daughter’s friends on social media so that she can keep tabs on them and has their modelling magazine covers proudly framed in her kitchen.
Yolanda moved from LA to a farm in Pennsylvania partly to be closer to her daughters who live in New York, and Gigi spent much of lockdown living at that home with her former beau Zayn Malik and their young daughter Khai.
Her influence and presence in Gigi’s life was widely said to be what sparked the confrontation which ended the model’s romance with Zayn when daughter Khai was only one year old.
It’s said that in October 2021, Yolanda dropped into the guest cottage at her farm where Zayn was living with Gigi and their daughter without giving notice and that in a confrontation which followed, he pushed her against a chest of drawers and shouted profanities.
He was charged with four criminal counts of harassment, all of which he pleaded guilty to.
The singer was subsequently sentenced to 360 days of community service — with 90 days for each charge — and he was also required to take anger management classes and attend an anti-domestic violence program.
The two separated shortly after his alleged assault of Yolanda, but they have continued to co-parent their daughter, and Zayn even visits Gigi and Khai at the Pennsylvania home sometimes.
Another hurdle that DiCaprio has to contend with if he hopes to woo Gigi will be her mother Yolanda, who is fiercely protective of both her daughters, previously describing herself as a ‘mama bear’
One inside source told me that Gigi is also reluctant to dive into another relationship after her ‘bad break-up’ from Zayn Malik, with whom she shares an infant daughter, Khai
Zayn 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.
Gigi’s five year romance with Zayn ended, it seems on the spot, and a lot of effort has been made to smooth out co-parenting since that point.
A friend in the modelling world says: ‘Gigi is a very mature 27. She spent years looking after Yolanda when she was so ill with Lyme 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 mom too. It wouldn’t surprise me if she was actually too grown up for Leo.’
DailyMail.com has reached out to representatives for Gigi and Leo for comment.
In an interview for NBC’s Sunday Sitdown this week Gigi said that she was besotted by her daughter Khai, saying: ‘I think she’s a genius. But I think that’s what everyone says about their kid. It’s so much fun. The more that she talks, and understands, and remembers, it just gets more and more fun. And she’s a blessing.’
Just weeks earlier, in July, DiCaprio was pictured enjoying an outing with Ukrainian model Maria Beregova, 22, during a trip to Saint-Tropez.
DailyMail.com revealed that Beregova had reverted to using her maiden name on the trip with DiCaprio after divorcing her husband Ahmed Masoud Abdelhafid, 30 — whose grandfather had served Libyan dictator Colonel Muammar Gaddafi.