Rag Time is a bi-weekly media investigation of a single celebrity story that's vastly more in-depth than you ever thought you needed. This week: Leonardo DiCaprio's constantly memed but never discussed romantic life.
In late May, Leo DiCaprio made his annual pilgrimage to the Cannes Film Festival, more commonly referred to as Cannes. The 44-year-old movie star goes every year, whether he has a movie to promote or not—this year, he was there for the premiere of Quentin Tarantino’s Once Upon a Time in Hollywood, which he stars in with Brad Pitt and Margot Robbie. But based on careful observation of his activities for the last several years, it seems like the main reason Leo goes to Cannes is to spend time with models, who congregate at the 12-day festival and on the very expensive yachts that surround it.
This year, Leo attended the festival with his girlfriend of a year and a half, a 21-year-old model named Camila Morrone. As is his custom, he didn’t identify her as his girlfriend to the press or walk the red carpet with her at any events. (She attended the premiere of OUATIH, but posed for photos on the red carpet separately.) He did spend some quality time with her in France, though, which we know thanks to The Daily Mail; the British tabloid published these remarkable photos of Leo and Morrone interacting after a lunch date at the exclusive Hotel du Cap-Eden-Roc. The headline: “Leonardo DiCaprio, 44, proves he's the ultimate Instagram boyfriend as he takes girlfriend Camila Morrone's, 21, photo during rare outing in Cannes.”
The photos provoked a wave of interest on social media because they depict Leo acting, well, actually interested in the woman he’s dating. Over the last two decades, he has dated dozens of mostly blonde models under the age of 25 (the rare exception being Blake Lively, a blonde actress who at one point had a Chanel contract). But he’s rarely acknowledged them in the media, or shown an excess of emotion for them in public. Remember Toni Garrn? Nina Agdal? Kelly Rohrbach? Erin Heatherton? Leo has appeared in the tabloids with all of them—hanging out on yachts in Europe, riding Citi bikes in New York—but he’s never talked about any of those relationships in the press. As a result, the public has come to take his affinity for young, almost-exclusively-blonde Victoria’s Secret and/or Sports Illustrated models for granted. He gets all of the benefits of being associated with young, attractive women, but he never has to explain himself when the relationships end, or when he starts dating literal teenagers. But when you look at the data, it’s jarring, which explains why this chart went viral on Reddit in March:
Leo keeps getting older, but his girlfriends stay the same age. And they never, ever talk about him in the press. How has he managed this careful balancing act for the last 20 years? Fire up your vapes and let’s take a leisurely bike ride down memory lane.
Meeting Models in Cannes
When he’s single, Leo goes to Cannes to meet new models. When he’s in a relationship, he brings whichever model he is dating, and also meets new models. Based on tabloid research, this trend started in 2011, when Leo attended the festival shortly after his breakup with then-25-year-old model Bar Refaeli. At the festival that year, he met and canoodled with then-23-year-old Lively on a yacht. (They had a brief affair, and then she dumped him for Ryan Reynolds.) In 2016, he met Sports Illustrated model Nina Agdal at the festival and started dating her, only to break up with her just a few days before Cannes the next year (she had just turned 24, which is perilously close to Leo’s apparent age limit for girlfriends—25). He attended the festival solo, and so did Morrone, then 19. They started officially dating six months later. (Morrone happens to be the former stepdaughter of Leo’s good buddy Al Pacino.)
Leo has never publicly discussed his strategy for meeting women, but according to one brave model who talked about it with Cosmo, he has it down to a science. In 2015, the women’s mag interviewed a group of Sports Illustrated swimsuit models and asked them about Leo. Model Ashley Smith said she watched Leo pick up a model at Cannes the previous year. "I saw him at a party. And he literally showed up, like, the most dressed down. He was in a baseball cap," she said. "Everyone else was in tuxedos, he came in a baseball cap, he was there for five minutes, found a girl, and left. You go, Leonardo! I wanted to give him a high five, but I didn't know him, so I didn't."
Of course, Cannes only happens once a year, so Leo has found ways to meet models stateside, too. In 2017, The New York Daily News published a fascinating report about how Leo was handling the club scene in the wake of the #MeToo movement. Here was the vibe at a Halloween party a few weeks after the first Harvey Weinstein stories broke:
“Partygoers at a lower Manhattan Halloween bash were left buzzing about the fact that Leonardo DiCaprio didn't approach any of the beautiful women at a 40-plus-person party that was stocked with models who appeared to be just his type. ‘He arrived with five friends, wearing a baseball cap, and talked to nobody outside of his group,’ according to one insider. ‘I mean no-bod-y.’"
We're told that even when DiCaprio's ‘ambassadors’ made the rounds, they very politely asked the women they met for their business cards, then went back to socializing with one another.”
Though the Daily News framed the report as Leo making a change in his behavior, it is well documented that he has used his friends to help him land models since he was in his twenties. (The "Pussy Posse" sprang into action at New York nightclubs in the '90s, and Leo's top lieutenants are still faithful to him after all these years: Here’s Tobey Maguire taking two young models to coffee with Leo in the fall of 2017, right before Leo started dating Morrone. Maguire, for what it’s worth, divorced wife Jen Meyer in 2016 and was last seen dating a 26-year-old … model.)
The Girlfriend Experience
So what happens to a model once Leo officially makes her his girlfriend? It’s not like he completely hides her away. In the last year and a half, paparazzi have gotten photos of Leo and Morrone hanging out on a yacht in Antibes, snorkeling in Positano, and sitting on the ground at Coachella. (Strangely, the couple has yet to be photographed riding Citi bikes in New York—one of Leo’s favorite summer date activities—but surely that’s coming.) Despite these public outings, Morrone, a budding actress who had a film of her own in Cannes this year, has never once discussed her relationship in an interview or posted about Leo on Instagram, where she has 1.7 million followers.
And at this point, journalists don’t even ask Leo about his personal life. (As far as I can tell, the last time Leo earnestly discussed “falling in love” in an interview was 1994.) These days, when he does do press, it tends to focus almost exclusively on his global warming charity work through the Leonardo Dicaprio Foundation, and his movies. This is probably due to some combination of sexism (leading men tend to get the “So when are you going to settle down and have kids?” question less often than their leading woman counterparts) and the fact that Leo employs a powerful Hollywood PR firm, Sunshine Sachs. The last time anyone directly asked him about his love life was an interview with Parade magazine in 2016. (He gave a short non-answer.)
It’s also long been rumored that women who date Leo sign some kind of non-disclosure agreement, as none of them have ever given tell-all interviews or gossipped about Leo to the tabloids after a breakup. (That’s a lot of people to keep quiet, especially in Hollywood.) While no reporter has ever gotten their hands on this kind of NDA, in 2017, the Los Angeles Times reported on NDAs that DiCaprio used to have employees sign at his production company Greenhour Corp. The agreements were “wildly overbroad,” said an expert, and prevented employees from disclosing any “confidential information” about Leo. “Confidential information, according to that document, includes information about the actor, his family and friends, his businesses and even ‘the existence of the contractor's business and/or personal relationship with DiCaprio,’” the Times reported. “The document goes on to say a long list of ‘offensive/inappropriate material’ is also confidential information.”
Whether or not Leo has the models in his orbit sign official agreements, most have been hesitant to ever discuss their relationships with him in the media. In the aforementioned Cosmo interview, the model Lily Aldridge, who never even dated Leo, visibly shut down when she was asked about him. Fellow model Gigi Hadid stepped in to say that Aldridge and Leo were friendly, but Aldridge herself did not comment at all and simply shook her head.
What Happens When Someone Breaks the Rules?
There have been very few occasions in which one of Leo's girlfriends has publicly shared information about their experiences with him. In the summer of 2013, Leo, then 38, was dating model Toni Garrn, and he hosted her 21st birthday party at his mansion in the Hollywood Hills. As young people do, some of her friends tweeted and Instagrammed photos from the party. Veteran gossip blogger Lainey Gossip then shared those photos on her site, before promptly receiving a request to remove them. Most of the friends who posted the photos quickly deleted them, though I found two that remain online—a group shot and a photo of Garrn's friend posing with Leo’s dog, Django.
A few months after the photo leak, Leo broke up with Garrn, and he was immediately seen leaving a Miami club with twenty women.
The only one of Leo’s ex-girlfriends who’s really talked about what it’s like to date him is his most famous (and therefore powerful) ex: Gisele Bündchen. And she waited 14 years to do it; the couple stopped seeing each other in 2005. In an interview with Porter magazine in February, she said that she broke up with Leo after she decided to cut back on partying to cope with her anxiety.
"No longer numbing myself with smoking, drinking and too much work, I was becoming more and more aware of things that I’d chosen not to look at,” she said. “Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes."
Leo has not responded.
Got a tip about this or any other celebrity mysteries? Email Allie at email@example.com, or contact her on Twitter.
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