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Leonardo DiCaprio Parties With Gigi Hadid In New York After Reportedly Saying He Wants To ‘Ditch’ His Playboy Reputation

May 7, 2023 by Maria Pierides

 
Splash News

This article has been updated since its initial publish date to include more information

Leonardo DiCaprio seems to have been a very busy man over the past month. Just weeks after being spotted with supermodel Irina Shayk, 37, at a Coachella after-party, the 48-year-old actor has sparked reconciliation rumors with old flame Gigi Hadid, as they both attended the same Met Gala after-party on Monday, May 1st. So juicy!

The pair arrived separately (a common celeb tactic!) at Zero Bond in New York City on Monday night, but their arrivals couldn’t have been more different if the paparazzi pictures were anything to go by. Gigi, who recently turned 28, was all smiles for the cameras as she was spotted in a stunning black ensemble after changing out of the custom sheer black Givenchy dress she wore to the Met Gala just a few hours earlier.

Also dressed in an all-black outfit, Leo attempted to hide his face with a black mask and a black baseball cap, but didn’t fool paps and fans as they spotted him in an instant! While we don’t know what happened inside the actual after-party, we suspect that Gigi and Leo *may* have at the very least spoken to each other, as sources revealed just last month that the pair still “hang out” when they can. Oh to have been flies on the wall!

Sources Say Gigi Hadid & Leonardo DiCaprio ‘Still Hang Out’

We thought that their brief relationship, which started after they got to know each other at New York Fashion Week in September last year, had run its course after sources reportedly told People back in February that the Guest in Residence founder was “done” with the Oscar-winning actor, and the romance had “fizzled” out. But in April 2023, an insider reportedly dished to Entertainment Tonight that Gigi and Leo “still hang out and talk when it works with their timing.” The source added, “They both enjoy each other’s company and have fun together when their busy schedules permit.”

Gigi’s famous family is supposedly supportive of their relationship, the source noted, pointing out that her mother, Yolanda Hadid, and younger sister, Bella Hadid, are behind her life decisions, including her romantic interests.”Yolanda and Bella know Gigi is capable of making her own healthy decisions and they’re supportive of her,” the source continued. “Gigi’s main priority is her baby girl. Her daughter is always top of mind and at the forefront of everything in her life.” As fans know, Gigi shares her two-year-old daughter Khai with 30-year-old ex-boyfriend Zayn Malik.

Insiders Previously Said Their Relationship ‘Fizzled’ Out

According to a February 17th People article, an insider said that the Vogue cover girl “hasn’t seen him for a while. She just decided that she was done with him,” in reference to the Don’t Look Up actor. The insider went on to say: “They are at very different places in life. She prioritizes being a mom. It was never that serious anyway. It kind of just fizzled.”

Gigi And Leo Tried To Hide When Spotted Together In Milan

Despite what the insider allegedly said, the pair were papped leaving Casa Cipriani Milano (separately, of course) in Milan on Thursday, February 23rd, just hours after Gigi walked the Prada runway during Milan Fashion Week.

The pair weren’t at Casa Cipriani Milano for a romantic one on one date though, as they were reportedly there with 20 mutual friends – including Kendall Jenner and Dakota Johnson to name just two – to celebrate British Vogue Editor-in-Chief Edward Enninful’s birthday. Were they mixing business with pleasure? We don’t know for sure, but here’s what we *do* know…

According to TMZ, Leo and Gigi were spotted sitting together and talking inside (what we would give to find out what they were talking about!) but things reportedly became “hectic” when they realized they had been spotted, with Gigi then trying to hide behind her bodyguard. A separate source told E! News that the Italian outing “was not a date,” adding, “They were in the same location at a party together. It was a dinner with 20 other people.”

Who Else Has Leonardo DiCaprio Been Linked To Recently?

The Wolf of Wall Street actor has been spotted with quite a few different ladies over the past year. DiCaprio recently came under fire for allegedly dating 19-year-old model Eden Polani, despite a source close to the actor *interestingly* saying that he wanted to ditch his Playboy reputation of dating young models.

But the Once Upon a Time… in Hollywood star didn’t seem to be succeeding, as he was spotted leaving celebrity hotspot Chiltern Firehouse with model Josie Redmond at 4 am on Wednesday, February 22nd. The Revenant actor kept a low profile as he left the London restaurant and hotel alongside the 21-year-old American model.

According to the Daily Mail, the Django Unchained actor is reportedly “not pleased” with the ongoing jokes about his love life, with a source previously saying he is desperate to “ditch” his playboy image of only dating women under the age of 25. DiCaprio also reportedly wants to settle down in a “more mature” relationship, with the source adding that he wants something “real”– much like the long-term romance he had with model Camila Morrone (who he broke up with when she turned 25!)

“Leo is very single right now and he is not keen on the hype suggesting that he is seeking out these very young women,” the source revealed to the Daily Mail at the time. “He is looking for something more mature in the relationship department. It is just ridiculous because he cannot go anywhere without being linked to the youngest beautiful woman there. He wants to ditch this image once and for all and he is really bothered that this continues to follow him. Leo wants something as he had with Camila, something real.”

For years now, DiCaprio has found himself the butt of many dating jokes. Many have pointed out that the actor apparently refuses to date a woman over the age of 25. The speculation about his dating habits has been exacerbated over the past year when DiCaprio split with Morrone just weeks after she turned 25. Then, he was photographed with a plethora of young models, including Polani (who at 19 is 29 years his junior!) and Lorenzo Lamas’ 23-year-old daughter Victoria Lamas.

DiCaprio & Hadid: A Timeline

Let's remind ourselves of Leo and Gigi's dating history too. Leo and Gigi were first linked in NYC on September 10th, 2022, when the Inception star and Vogue cover girl attended a New York Fashion Week afterparty held at the exclusive private member club Casa Cipriani. This was just a few weeks after DiCaprio called it quits with Morrone.

On September 21st, a source reportedly told People that Hadid and DiCaprio "like each other and are having a good time." Another source supposedly close to the pair added that the Great Gatsby alum is very "taken with Gigi," explaining that she is the "type of woman he is usually attracted to."

The insider went on, "They sort of run in the same high profile circles and would see each other at events, clubs, restaurants and gatherings." At the time, the source added that DiCaprio and Hadid weren’t "serious," saying, "Leo has not been out of his relationship with Camila long enough to jump headfirst into anything. I am not sure he is completely finished with Camila. That was a long romance."

Page Six reported in early November that the Don’t Look Up actor and the catwalk model attended Circoloco’s Halloween party together along with her sister, Bella Hadid, fellow model Irina Shayk, and art dealer Helly Nahmad at the Brooklyn Navy Yard. They arrived by party bus, the outlet noted, with a source saying that "Leo wore a [scary] mask most of the night unless he was drinking," and "the group got bottle service."

They were also photographed by paparazzi on November 19th as they left a dinner date at Cipriani and covered their faces as security guards rushed them out of the restaurant. The duo also dined with venture capitalist Vivi Nevo, a close friend of the Titanic actor.

When the rumors of Gigi and Leo dating came out, a source allegedly told Entertainment Tonight that the model’s family approves of DiCaprio, specifically mentioning her younger sister Bella and mother Yolanda. "Bella and Yolanda think Leo is incredibly talented and are of course supportive of their relationship," the insider said, adding that "they just want Gigi to be happy, support her, and help her be a great mom" to her daughter Khai.

Another source echoed this, reportedly telling People that Gigi was having "fun dating Leo," but her "first priority is being mom." They continued, "She seems very happy and excited about seeing him. She is attracted to him. He treats her really well. She finds him mature and charming."

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