The pair were first photographed at a New York Fashion Week party in conversation. DiCaprio, wearing a hat, was seen holding hands with the model who is 20 years his junior. Word is they’re “dating” but “keeping it casual.” So well-known are DiCaprio’s dating preferences that earlier this week it was the running 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 and a serial dater of young bikini models, is hooking up with 27-year-old Gigi Hadid has raised eyebrows in Hollywood. It is true that in the last two decades one young model succeeded another in an endless model. But has he ever mocked an Oscar-winning star so openly and personally? And while model Gigi wonders if their “fun” and “casual” date could turn into a more serious romance, she doesn’t really need to listen to the chatter of the wider world to find out about her beau — as she can rely on plenty of advice from closer to home. And how well informed it will be. Because, in a delicious twist, it turns out that Gigi is friends with at least SIX of DiCaprio’s ex-girlfriends (all of whom are 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. Unfortunately for DiCaprio, it’s hard to imagine his exes giving advice Gigi that the Leo plus one life is a lot of fun. A modeling source said: “He’s fishing in a small pond and it got to the point a while ago where all the models know him and all the models have dated him. I would say that the situation is not really in his favor.’ Gigi Hadid’s best friend among his clan of exes is actress and model Blake Lively — who has been the face of Dior and L’Oreal. She and Gigi have been close since around 2014, when they were both part of singer Taylor Swift’s so-called girl group. A deep friendship has developed and the pair have been seen hanging out at fashion shows, the Met Gala Ball and concerts and dinners in New York. Lively, who is married to actor Ryan Reynolds and just announced she is pregnant with their fourth child, gave Gigi advice on raising her daughter Khai, two. Khai is Gigi’s child with former One Direction star Zayn Malik, who she split from last October. Both Gigi and Blake opened up about their relationship 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 her world. . . I’m grateful for what he shares, but I also understand the boundaries he chooses to set.’ Because, in a delicious twist, it turns out that Gigi is friends with at least SIX of DiCaprio’s ex-girlfriends (all of whom are also models, of course) Last year, Blake wrote two Instagram posts to celebrate her friend’s birthday, sharing a video of Gigi dancing with the loving caption: “Too bad you’re so hot and not having any fun.” 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 make a much better couple.” Blake, 35, dated DiCaprio for five months from May 2010 to October 2011. They had previously met when Blake was auditioning for a role in The Great Gatsby, and were spotted together at Disneyland, in Monte Carlo, New York and Sydney. They seemed happy, but broke up abruptly after Blake visited DiCaprio in Australia, where he was filming Gatsby. Reports say that he unexpectedly cut her off and that she was broken for a while. He then linked up with model Madalina Ghenea, whom he also met while in Australia. Another former love of Leo is the blonde German model Toni Garrn. They were an item in 2013 and 2014, traveling to Cannes and Bora Bora — and were spotted kissing and cuddling in 2017 when they were back ‘among the models’. Why did the romance end? Well, it all went south just days after DiCaprio was spotted leaving the Art Basel show in Miami sporting a beard and man bun and “with an entourage 20 women deep.” It’s doubtful, then, that Tony will advise Gigi to do so. Tony has known Gigi for years, they actually became friends in 2014 around the time Tony first broke up with DiCaprio. Spotted chatting together on the front row of a fashion show in 2015, Gigi was one of Toni’s biggest supporters when she launched a charity in 2016 to support women and girls in Africa. The Toni Garrn Foundation holds an annual ‘Supermodel Flea Market’ and Gigi has donated up to 100 garments a year for it. Both women are also Victoria’s Secret Angels, although Toni quit the shows the year before Gigi donned the famous wings, saying she was asked every year to lose more weight and simply found the demands impossible. Toni quickly found herself replaced in Leo’s affections by blonde swimsuit model Kelly Rohrbach (Kelly and Gigi also know each other, of course). Perhaps the most famous former flame is supermodel Gisele Bundchen. They met in 1999, when she was just 18. DiCaprio apparently saw her on a catwalk and called her agency to get her phone number. Their six-year relationship was their longest to date, with the couple splitting in 2005. However, before the year was out, he was with model Bar Rafaeli, who, in appearance, could be Gisele’s younger sister. He must have been injured. Gisele said in an interview that she wished DiCaprio but ended it because she wanted to do “serious soul searching” and he didn’t. Although 15 years her senior, Gisele was something of a mentor to Gigi, who was among those invited by Chanel to celebrate Gisele becoming the face of Chanel No 5 fragrance 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 his clan of exes is actress and model Blake Lively — who has been the 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 called a dig — she was quick to apologize for it all. The other “Leo” models Gigi knows are friends through work — through ad campaigns, including one for Sports Illustrated. Is it okay that he only dates models, and that they all know each other? So far, Gigi has not been postponed. A source says: “Gigi and Leo have hung out many times and are into each other. Gigi thinks he’s a really nice guy.’ They’ve known each other socially for years — on the party modeling circuit — and the story goes that I 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 Morone was over. Since that party he’s apparently been chasing Gigi — he was seen with her again at The Ned in August. The daughter of wealthy property developer Mohamed and ultra-ambitious Dutch model Yolanda, Gigi grew up to be a model and was pushed on a diet and driven to the top by her mother, who told her she was eating birthday cake and discouraged her. an enthusiasm for basketball so as not to make Gigi seem less feminine. A source says: “Gigi is still fresh from a very nasty break-up [with Zayn Malik] plus Leo has a reputation. We’ll see. But she’s a smart girl and she’ll look before she leaps.’ And you have to wonder what Gigi Hadid’s terrible mother who has been married and divorced twice herself will think. Calling herself a “mama bear,” she’s fully involved in the lives of Gigi and Bella’s daughters, and sources say Yolanda will be the gatekeeper if Gigi decides the fling will mature into true romance. Her influence and presence in Gigi’s life is widely said to be what sparked the conflict that ended her romance with Malik when her daughter Khai was just one year old. In October 2021, Yolanda dropped by the guest cottage on her farm where Malik was staying with Gigi and their daughter without giving notice. In an ensuing confrontation, Malik allegedly pushed Yolanda into a dresser and yelled profanities. A source says: “Gigi is still fresh from a very nasty break-up [with Zayn Malik] plus Leo has a reputation. We’ll see. But she’s a smart girl and she’ll look before she leaps.” He was charged with four counts of harassment, pleading guilty to one and no contest to the other three. He was then sentenced to 360 days of community service, ordered to take anger management classes and attend a domestic violence program. He and Gigi broke up shortly after the incident, but continued to raise their daughter together, and Malik visits her and Khai at her home in Pennsylvania. Malik said in a statement that he had not hit Yolanda, but chose not to fight the charges to protect his daughter from the publicity a court case would bring. A friend in the modeling world says: “Gigi is a very mature 27. She spent years taking care of Yolanda when she was sick with Lymes disease and taking her to the hospital when she had flare-ups. Then she became very involved with Zane,…