By Stacy Lee Kong

Before we get into all of… this, I just want to start by stressing that I am fully here for jokes, both in general and specifically about problematic dudes, who 100% deserve to be laughed at. But at the same time, I’ve been thinking about what it means when something—like, you know, Leonardo DiCaprio’s dating habits—becomes a common thing to joke about, and how that can change the way we actually talk about it… and maybe even help normalize it.

For example! The internet spent much of this week speculating about whether DiCaprio (48) was dating Israeli model Eden Polani (19). A source denied they were coupled up to People, saying, “Leo and Eden just so happened to have been seated next to each other at the party, and were hanging in the same group… Just because Leo might be talking to or sitting with a girl doesn't mean he's dating her.” But dating much younger women is kind of Leo’s thing, right? So obviously, an anemic denial from an unnamed source really didn’t do much to stem the tide of snarky takes about what seemed like the latest example of his usual behaviour. Twitter users pointed out that DiCaprio and Polani are basically the same ages as The Last of Us stars Pedro Pascal and Bella Ramsey and Stranger Things’ David Harbour and Millie Bobby Brown, which is wild because both duos portray a father/daughter relationship onscreen. Lots of people shared their opinions about the actor’s dating habits specifically, and age gaps in relationships in general. And just about every entertainment-focused publication covered what people were saying online.

Of course, this isn’t the first time we’ve seen this discourse, but I’m belatedly realizing how weird it is that those conversations are almost always kind of… jokey? To be fair, sometimes this is a purposeful decision intended to make a sharp point, as in The Cut’s take this week, which uses humour to argue that DiCaprio dating a literal teenager is very much in keeping with his pattern. “Honestly, it’s like every time he sits next to a woman under the age of 25 or talks to her or takes her to the mall, people assume the worst — that he is a gross old lech,” wrote staff writer Claire Lampen. “Today, for example, the Daily Mail reported that Leo might be seeing a 19-year-old model named Eden Polani, and for some reason, many readers just accepted that as plausible, predictable, and probably true, which — rude! Leo is single. He has been so since breaking up with his last girlfriend shortly after she turned 25.” Perfection.

But a lot of times, there wasn’t a point to be made, just a weird attempt to co-opt a conversation for marketing purposes. For instance:

Sorry not sorry, but something about government-run environmental organizations using predatory behaviour in their little social media jokes just makes me uncomfortable, you know?

A short history of Leonardo DiCaprio breaking up with women as soon as they turn 25

And it is predatory, to be clear. If you haven’t seen the chart that breaks down exactly how/why, please allow me to introduce you this masterpiece of data visualization:

Designed by Reddit user TrustLittleBrother in 2019 and updated in 2022, the data in this chart is slightly out of date (for example, it doesn’t include DiCaprio’s rumoured romance with Gigi Hadid, who was 27 when they were linked late last year), but it does an excellent job of illustrating the actor’s overall romantic preference for young, thin, mostly white models. The cliché that he keeps getting older and they stay the same age very much applies; almost every relationship ends when they turn 25, if not before. And sometimes, he meets them when they are very, very young. His most recent ex, Camilla Morrone, was 20 when they met in 2017. He was with Toni Garrn from 2012 to 2013; they met when she was 20. He and Bar Rafaeli dated from 2004 to 2009; she was also 20 when they met. And he started dating Gisele Bundchen in 1998 when she was 18. He has also been linked in the past to models Candice Blackburn (then 20) and Juliette Perkins (then 19).

To be fair, he was 24 when he was dating an 18-year-old Bundchen, so there was much less of an age gap, but he was 30 when he got together with Rafaeli, 38 when he started dating Garrn and 43 when he and Morrone met. I don’t want to undermine these women’s autonomy, not am I saying every May-December romance is predatory—I don’t think we need to worry about Holland Taylor (80) and Sarah Paulson (47), Cher (76) and Alexander Edwards (36), George (61) and Amal (45) Clooney or Priyanka Chopra Jonas (40) and Nick Jonas (30), you know?—but I think it’s fair to be suspicious of the ones that start when one party is firmly in middle age and the other’s prefrontal cortex, AKA the rational side of their brain, has not yet fully developed. And that’s especially true when there’s a profound power differential. I made this point when I wrote about Scott Disick’s very similar dating habits, but to me, the problem here is not just that DiCaprio is older than his partners; it’s that for more than two decades, he has chosen to exclusively partner with really young women who have significantly less social, professional, political and financial power than him. That’s not a guarantee that his relationships are abusive, obviously, but it’s not a great sign.

As Daria J. Kuss, a psychologist and associate professor of psychology at Nottingham Trent University, told Cosmpolitan UK in December in a story inspired by another age gap romance, this one between 21-year-old Billie Eilish and 31-year-old singer-songwriter Jesse Rutherford, “in some relationships where there is a significant age gap between partners, for example 10 years or more, there may be unique problems the couple can face, including power imbalances. In some cases, coercion and financial control may be a reason for confrontation. Age may make younger partners more vulnerable with regards to being more dependent on the older partner.”

Even if DiCaprio has never engaged in coercion or financial control, it’s difficult to imagine why he would consistently choose the partners with less lived experience and status than him if that wasn’t part of the attraction, and that alone is predatory.

So why do we have such a hard time calling his behaviour what it is?

I think on some level we recognize that. But very few people actually come out and say it, and it’s worth questioning why. What protects DiCaprio from widespread censure for what seems like a pretty obvious case of powerful-white-dude-being-gross-about-women, especially in a post-#MeToo world? (Aside from his whiteness, maleness and the fact that there are limits to #MeToo’s impact, of course.)

One Twitter user has speculated that “one of the reasons leonardo dicaprio gets away with his predatory shit is bcos a lot of legacy media ppl still see him as that hot kid from the 1990s and not a gross creepy dude approaching 50” and I can see where they’re coming from. After all, when director Sam Taylor-Johnson (43 when they met) and actor Aaron Taylor-Johnson (either 18 or 19; reports vary) went public with their relationship in the early 2010s, women’s magazines were pretty celebratory, as if a woman engaging in the same predatory behaviour that we usually see from men was a feminist victory. Now, the staff at entertainment-focused legacy media outlets are just the right age to have fallen for Leo in The Basketball Diaries, Romeo + Juliet and Titanic, so sure, maybe they’re still envisioning him as the heartthrob of their youth and it doesn’t feel like he’s pushing 50.

But I think what’s more likely going on is that this all seems normal. This week, Phoebe Maltz Bovy, senior editor at The Canadian Jewish News, argued that while she doesn’t know if there’s any truth the rumour that DiCaprio and Polani were dating, what she “can state with confidence is that the famous and famously handsome actor enjoys dating beautiful young women. News at 11, as the saying goes. He can, and like so many would if they could, he does.” This is misguided and weirdly dismissive, but she’s not wrong, about this at least; rich, famous men have always used their status to land young, beautiful partners because these are the people our society perceives as most desirable for a variety of weird and problematic reasons. Plausible deniability is at play here, too. His approach to relationships is morally questionable, but not illegal, so it feels like a grey area—and that makes it easier for people to look away from the implications of his dating choices, especially if they like his work or enjoy his public persona.

And I think the joking helps make it seem even more normal. People have largely communicated their discomfort with DiCaprio’s dating history through humour—at its core, the girlfriend age chart is basically well-designed snark, right? And while that can be effective, the very act of joking about it almost positions it as a charming flaw, an easy shorthand for ‘what men really want’ or the kind of thing that would prompt you to say “Oh, that’s Leo! What can you do?” like always being late or tipping badly. The quip ends up neutralizing the point it was trying to make.

What’s more, I’d argue that those jokes have recently lost whatever sting they might have once had. I mean, it’s gotten to the point where award show hosts use his much-younger girlfriends as fodder for their opening monologues, which might just be the least edgy form of comedy ever. Last year, Amy Schumer joked about DiCaprio making climate change his cause because he wants to “leave behind a cleaner, greener climate for his girlfriends,” at the Oscars, while Kenan Thompson wished Zendaya a happy birthday at the Emmys by saying, “Zendaya just turned 26 last week, happy birthday. 26 is a weird age in Hollywood. I mean, you're young enough to play a high school student but too old to date Leonardo DiCaprio.” Which is basically the same joke comedian Ricky Gervais made in his Golden Globes opening monologue in 2020, when he said, “Leonardo DiCaprio attended the premiere [of Once Upon A Time In Hollywood], and by the end his date was too old for him… Even Prince Andrew was like, 'Come on mate.’”

Clearly, Hollywood doesn’t have that much of a problem with DiCaprio’s behaviour if they’re laughing about his sketchy behaviour at the major industry events they keep inviting him to. (Also, Schumer reportedly checked to make sure DiCaprio would be okay with her joke ahead of time, which I think was supposed to show how easy-going and cool he is, like ‘Look! He can take a joke!’ but to me is just more evidence of how much power this guy has.)

If the reply guys are any indication, the jokes aren’t working like we thought they would

The other part of why the jokes aren’t landing for me is definitely the state of the internet right now. We keep hearing about how podcast bros and men’s lifestyle influencers like Andrew Tate are inducting an entire generation of young men into what basically amounts to a cult of toxic masculinity. Tate proudly advises other men to be violent, aggressive and controlling. He has said he prefers to date women who are 18 or 19 so he can “make an imprint” on them. He moved from the UK to Romania because “rape laws are more lenient there”—though joke’s on him, since he’s still being detained by Romanian authorities on charges of organized crime and sex trafficking. And while he popularized this attitude, it’s not just Tate; I cannot actually count the number of times I saw that one dude on TikTok talk about how he doesn’t want to date women in their 30s because they’re no longer “impressionable.”

This is an entire movement aimed at undermining women’s autonomy in relationships and selling men on the myth that they will feel fulfilled, secure and happy if they are in control of their partners, instead of seeking out equitable relationships where they can give and receive genuine care, compassion and love. And it’s targeting youth, so we really can’t cling to the idea that the kids will be okay because the bigots will eventually die out; the kids are unfortunately being indoctrinated into these same cycles of hate and prejudice. You can tell be the number of men who reply to any mention of DiCaprio’s partner’s ages by insisting it’s technically legal to date a 19- or 20-year-old, as if laws have always been a perfect barometer of ethics or morals. It’s extremely depressing! And also dangerous! In that context, it just feels super weird to downplay DiCaprio’s actions or soften the way we speak about them, even joking-not-jokingly.

So… to go back to what I said at the beginning of this newsletter: I’m here for humour. I’ve enjoyed all the people mocking DiCaprio for being so incredibly predictable, and I think in some cases it has been an effective way to signal disapproval, or at least call attention to his behaviour. But now the stakes feel higher and the jokes a bit more stale, so I wonder if we need to revisit our strategy.

Maybe we just call him a predator instead.

And Did You Hear About…

This beautifully written personal essay by Niko Stratis about going to bible camp as a kid who was trans long before a word told her she could be.

Director Gina Price-Bythewood’s Hollywood Reporter article on “the consistent chasm between Black excellence and recognition,” in which she reveals that she’s producing a movie and the executives insist on hiring a Black Oscar-winning director… only, a Black person has never won Best Director.

This on-point—but also hilariously blunt—analysis of the vanilla-hued, Pilates-loving, claw clip-wearing aesthetic that’s on the rise, and why it’s actually about “white girl soft power.”

Canadian skating star Jamie Salé’s descent into COVID conspiracy theorist and right wing media darling.

Writer Danyel Smith’s gorgeous profile of Sza.

The extremely awkward photos from Reese Witherspoon and Ashton Kutcher’s press tour for their new romcom, Your Place or Mine, and far more importantly, this Twitter thread of red carpet moments where other actors’ chemistry is… so much more apparent.

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