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Why Older Men Date Younger Women: A Defense of DiCaprio

By Don Hall

Seriously, have you met women in their forties and fifties?

They're smart. They've had life experience and frequently have finely honed bullshit detectors. There's an element of bitterness in there that indicates they've been done wrong by men more than a few times. They know what they're looking for in a man and most of us are found to be lacking.

They're picky. They're focused. They're demanding. All, in part, due to living with men who came up short (which is why they're single or looking to get some strange from struggling marriages).

Dating a woman in her forties or fifties is like dining with an incredibly specific eater.

"I'd like salad with the dressing on the side, hold the tomatoes. My burger needs to be exactly medium rare and the bun cannot have any seeds and should be fresh. The french fries have to be crispy on the outside but pillowy on the inside. Oh, and for my date, he needs to be intellectual but not arrogant, funny but not at the expense of others, financially secure but not a workaholic with the porn addiction on the side, please."

On the other hand, you have young women under the age of twenty-five. Twenty-five is a scientific milestone for all humans. It’s when the development and maturation of your prefrontal cortex, the part of the brain responsible for impulse control and decision-making, is finally complete. These women have just barely reached maturity and their brain is finally fully formed with that new car smell.

Leonardo DiCaprio seems to enjoy the ladies uncomplicated by the rough edges life tends to create, looks for company less scarred by bad relationships, and particularly digs the pretty model-types. Keep in mind, the models are breed of their own in that early narcissism is at an all-time high among them. They make a living by being looked at, being fetishized. Their power in life comes from the very gaze the hairy-legged feminists despise.

Note, I am myself a hairy-legged feminist but I'd guess I'm more Second Wave than insane and full of spite.

So, what's the issue with Leo's proclivity and preference for women between twenty and twenty-four? First, I'd guess it's his consistency:

DiCaprio is the Wooderson of Hollywood ("I keep getting older and they keep staying the same age.") and, for some reason, lots of people have an issue with this. He's creepy. He's a dirty old man. He should date women his own age as if his next girlfriend will end up being a forty-six-year-old IHOP waitress in need of a gym membership.

This all makes a sort of moralistic sense except for two dilemmas these angry, tsks-tsking folks need to acknowledge:

First, the women he dates are in the business of dating older, wealthy men. That's their job like a high-end escort or Russian bride (you think Melania Trump was into the fat ass known as Donald?) Their instagrams are designed to appeal to GenX dudes with a hard-on. Their Tik Toks are crying out for sugar daddies. Their OnlyFans are created specifically to squeeze out tips from guys who dig the youngsters in bikinis. Of course, he's going date these young women—they advertise their availability every day.

Second, you don't get to have it both ways, gang. Either these young women are strong, intelligent activists with agency and the ability to parse out consensual sex or they are children unable to make legitimate decisions about who they date or note because their prefrontal cortex renders them blithely ignorant of the horrors of an older dude's saggy balls. You can't argue that they are responsible adults and should be taken seriously when they gather in the streets for a cause and then loot and pillage and, at the same time, argue they're too young to be taken seriously when an old, wealthy Hollywood star wants to shack up for a few years.

In 2013, I dated a woman twenty-one years younger than I was at the time. She was twenty-six years old. Her father and I were the same age. We danced around the sexual tension for a bit until I went for it. She told me that she had seen me onstage a few months before and told her friend, "I'm gonna fuck that guy. Not fall in love but absolutely fuck him."

That's exactly what she did. I got the feels, she didn't. She reminded me when she was pretty done with our three month dalliance that I was as old as her father. That it was “not cool.” I didn't take it well because (and here's the kicker and the best defense of Leo) I didn't feel forty-seven. My body was forty-seven. My mind was as well. But I still felt like I was thirty years old. Perhaps it's a consequence of our perpetual adolescent society or the breakdown of family or maybe even the elimination of legacy jobs in corporations. Whatever the cause or causes, I didn't feel old.

In fact, I didn't feel old until she reminded me how old I was. My third ex-wife was fourteen years my junior and it was a sport of hers to remind me of my age on the regular. Age isn't relative. You are exactly as old as you are. What that age means in terms of what you can accomplish or who you can hump is minimal.

Finally, who cares who DiCaprio dates as long as they are legally of age in the state he's dating her in? Blame not the younger woman looking to date the ridiculously wealthy guy who hasn’t become a wrinkly sack of mush because most of the men her own age are spineless soyboys. Blame not the old man dating the youngest, prettiest, least demanding women he can find anymore than you'd blame him for buying a new car or getting the latest iPhone model.

Funny that, no one knows what car Leo drives or which smartphone he has.