Why We’ll Never Get Tired of Jokes About Leonardo DiCaprio’s Age-Gap Relationships

On Sunday night, Oscar's co-host Amy Schumer made a joke that never seems to get old

Leonardo DiCaprio attends the "Don't Look Up" World Premiere at Jazz at Lincoln Center on December 05, 2021 in New York City.
Leonardo DiCaprio is famous for many things, including dating younger women.
Dimitrios Kambouris/Getty Images for Netflix

Last night, Oscar’s co-host Amy Schumer cracked a joke people have been making for at least a decade or so. “I mean, Leonardo DiCaprio — what can I even say about him? He’s done so much to fight climate change and leave behind a cleaner, greener planet for his girlfriends,” the comedian quipped while co-hosting Sunday night’s event.

Schumer knew her joke wasn’t terribly original, sarcastically explaining it back to the audience: “Because he’s older, and they’re younger. You get it.” Again, people have been making some version of this joke for as long as DiCaprio has been old enough to be considered significantly older than the string of 20-something women he’s famously dated, and it always lands.

While men in Hollywood (and of course, men in general) dating significantly younger women is obviously nothing new, DiCaprio is certainly the most famous of his time. These days, the star’s penchant for dating younger is as much a part of his image as his numerous A-list roles, relative lack of Oscar wins and climate activism. At this point, a joke about Leonardo DiCaprio dating younger women is less a joke about Leonardo DiCaprio, the women in his life or even age-gap relationships in general than it is a joke about the joke, an allusion to the broad canon of Leonardo DiCaprio age-gap relationship jokes with the which the audience is obviously aware.

It’s a joke we’re all in on, but, as is true of all jokes, there will always be those who don’t get it. For the past three years, my pinned tweet has read: “An important milestone in every young woman’s life is the day she realizes she’s older than Leonardo DiCaprio’s current girlfriend.” Like most Leo age-gap jokes, it has performed relatively well, but over the years my replies have filled with pushback from men who felt compelled to come to DiCaprio’s defense. There are those who have questioned why I don’t instead take aim at “whichever ‘boytoy’ Madonna is dating,” those who accuse me of misandry and, of course, those who simply hurl sexist slurs and tell me I’m “too dumb and ugly to make it in porn,” which, while probably true, doesn’t feel particularly relevant.

What these men are missing — besides the fact that I have devoted a significant portion of my work to defending age-gap relationships, informed by my personal experience as a woman who has consistently dated significantly older men myself — is that this joke is not one at Leonardo DiCaprio’s expense, but rather my own.

It’s an uncomfortable reality that a woman’s sexual market value (and, arguably, value as a human being in society, period) declines much earlier and much more sharply with age than a man’s does. Not typically one to fight against an unfair system but rather leverage it to my advantage, I’ve elected to lean into this particular gender inequality, figuring I might as well make the most of my youth while I have it and date older men while I have the chance. (This, of course, might make me “part of the problem,” something I have explored at length elsewhere.) Still, dating older men in your 20s won’t stop you from eventually aging out of their interest. No matter how big the age gap, most women will still age “faster” than the men they are dating. Not all men will break up with their younger partners the day they hit 30, of course, but most women still grapple with the reality that no matter how young they are or how old he is, there will always be someone younger to take their place. I don’t blame men for wanting to date younger women, but just because I’ve accepted the terms doesn’t mean I like the future that awaits me.

In the meantime, as I wait for the inevitability of age to render me a virtual nonentity as a woman, it can be helpful to joke about it. To be sure, there are certainly plenty of women who do criticize men, particularly those in the public eye, for dating younger women, so I can understand some of the male defensiveness surrounding Leo age-gap jokes. But when women make this joke, and it is usually women making it, I believe it is usually playfully self-deprecating — a way of processing the uncomfortable reality that we will one day, through no fault of our own, age out of society’s good graces while men are left to ripen like fine wine.

We’re all in on the Leo age-gap jokes, but in different ways. For men, it’s a reminder of your own privilege, a joke that lets men of all ages bask in the comforting knowledge that they could have sex with younger women any time they want to. For women, it’s a self-deprecating joke that bonds us together against the sexist, ageist forces of a society that is stacked against us, a reminder that no matter how young we may be, we too will one day, not so very long from now at all, age out of Leonardo DiCaprio’s theoretical dating pool. It is also a reminder to women to neither pride ourselves too much on our youth, nor beat ourselves up too much about our age. We are only on one side of the Leonardo DiCaprio age limit until we are on the other. There’s nothing we can do about it but make jokes.

Win the Ultimate Formula 1® Crypto.com Miami Grand Prix Experience

Want the F1 experience of a lifetime? Here’s your chance to win tickets to see Turn 18 Grandstand, one of Ultimate Formula 1® Crypto.com Miami Grand Prix’s most premier grandstands!